# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_I
_database_code_depnum_ccdc_archive 'CCDC 1872657'
loop_
_audit_author_name
_audit_author_address
'Mustafa Can TASKAN, Ercan DUYGULU, Sevde DEMIR, Fatma YUKSEL'
;Gebze Technical University
Turkey
;
_audit_update_record             
;
2018-10-11 deposited with the CCDC.	2020-03-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C13 H11 Br3 N2 O'
_chemical_formula_sum            'C13 H11 Br3 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         450.97

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4706(6)
_cell_length_b                   7.4628(7)
_cell_length_c                   16.4827(16)
_cell_angle_alpha                93.785(7)
_cell_angle_beta                 94.273(6)
_cell_angle_gamma                104.845(6)
_cell_volume                     764.23(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4110
_cell_measurement_theta_min      2.8348
_cell_measurement_theta_max      24.0539
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.073
_exptl_crystal_density_diffrn    1.960
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432

_exptl_absorpt_coefficient_mu    7.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.40
_exptl_absorpt_correction_T_max  0.60

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            11028
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_theta_min         1.24
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             2687
_reflns_number_gt                2150
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1086
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_number_reflns         2687
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+1.5250P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.686
_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 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'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL V6.14 (Bruker AXS)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7244(7) 0.9514(7) 0.8237(3) 0.0460(11) Uani d . . . 1 . .
H H1A 0.7116 1.0243 0.7779 0.055 Uiso calc U . R 1 . .
H H1B 0.8164 0.872 0.8099 0.055 Uiso calc U . R 1 . .
C C2 0.5033(9) 0.7138(8) 0.9081(3) 0.0530(13) Uani d . . . 1 . .
H H2A 0.3607 0.6316 0.9091 0.064 Uiso calc U . R 1 . .
H H2B 0.5338 0.797 0.9578 0.064 Uiso calc U . R 1 . .
C C3 0.5029(7) 0.8291(6) 0.8353(3) 0.0403(10) Uani d . . . 1 . .
C C4 0.3447(8) 0.9443(7) 0.8535(3) 0.0502(12) Uani d . . . 1 . .
H H4A 0.3974 1.0222 0.9041 0.06 Uiso calc U . R 1 . .
H H4B 0.2078 0.8604 0.8617 0.06 Uiso calc U . R 1 . .
C C5 0.4341(7) 0.7078(7) 0.7558(3) 0.0435(11) Uani d . . . 1 . .
H H5A 0.4387 0.7846 0.7104 0.052 Uiso calc U . R 1 . .
H H5B 0.5303 0.6289 0.7479 0.052 Uiso calc U . R 1 . .
C C6 0.1231(8) 0.4815(6) 0.6927(3) 0.0412(10) Uani d . . . 1 . .
C C7 -0.0890(8) 0.3782(7) 0.6972(3) 0.0457(11) Uani d . . . 1 . .
H H7 -0.1545 0.3895 0.7449 0.055 Uiso calc U . R 1 . .
C C8 -0.2009(8) 0.2610(7) 0.6323(3) 0.0464(12) Uani d . . . 1 . .
H H8 -0.3413 0.1928 0.6363 0.056 Uiso calc U . R 1 . .
C C9 -0.1058(8) 0.2433(6) 0.5607(3) 0.0417(11) Uani d . . . 1 . .
C C10 0.1063(7) 0.3448(6) 0.5562(3) 0.0385(10) Uani d . . . 1 . .
C C11 0.2199(7) 0.4639(6) 0.6213(3) 0.0421(11) Uani d . . . 1 . .
H H11 0.3604 0.5319 0.6174 0.051 Uiso calc U . R 1 . .
C C12 0.2059(8) 0.3271(7) 0.4815(3) 0.0479(12) Uani d . . . 1 . .
C C13 -0.2211(8) 0.1259(7) 0.4908(3) 0.0500(12) Uani d . . . 1 . .
N N1 0.2814(8) 0.3122(7) 0.4223(3) 0.0685(14) Uani d . . . 1 . .
N N2 -0.3107(8) 0.0353(8) 0.4343(3) 0.0725(14) Uani d . . . 1 . .
O O1 0.2178(5) 0.5948(5) 0.75954(19) 0.0498(8) Uani d . . . 1 . .
Br Br1 0.29963(11) 1.10053(10) 0.76888(4) 0.0730(2) Uani d . . . 1 . .
Br Br2 0.86213(9) 1.12043(8) 0.91905(3) 0.0629(2) Uani d . . . 1 . .
Br Br3 0.70892(13) 0.56520(10) 0.90828(4) 0.0783(2) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C3 . 1.523(6) ?
C1 Br2 . 1.952(5) ?
C1 H1A . 0.97 ?
C1 H1B . 0.97 ?
C2 C3 . 1.523(6) ?
C2 Br3 . 1.938(5) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 C5 . 1.511(6) ?
C3 C4 . 1.529(6) ?
C4 Br1 . 1.928(5) ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C5 O1 . 1.445(6) ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C6 O1 . 1.347(6) ?
C6 C11 . 1.388(6) ?
C6 C7 . 1.402(7) ?
C7 C8 . 1.367(7) ?
C7 H7 . 0.93 ?
C8 C9 . 1.386(7) ?
C8 H8 . 0.93 ?
C9 C10 . 1.397(6) ?
C9 C13 . 1.434(7) ?
C10 C11 . 1.379(7) ?
C10 C12 . 1.446(7) ?
C11 H11 . 0.93 ?
C12 N1 . 1.135(6) ?
C13 N2 . 1.138(7) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 C1 Br2 . . 114.3(3) ?
C3 C1 H1A . . 108.7 ?
Br2 C1 H1A . . 108.7 ?
C3 C1 H1B . . 108.7 ?
Br2 C1 H1B . . 108.7 ?
H1A C1 H1B . . 107.6 ?
C3 C2 Br3 . . 114.5(3) ?
C3 C2 H2A . . 108.6 ?
Br3 C2 H2A . . 108.6 ?
C3 C2 H2B . . 108.6 ?
Br3 C2 H2B . . 108.6 ?
H2A C2 H2B . . 107.6 ?
C5 C3 C1 . . 104.5(4) ?
C5 C3 C2 . . 111.8(4) ?
C1 C3 C2 . . 113.0(4) ?
C5 C3 C4 . . 111.7(4) ?
C1 C3 C4 . . 111.9(4) ?
C2 C3 C4 . . 104.1(4) ?
C3 C4 Br1 . . 114.2(3) ?
C3 C4 H4A . . 108.7 ?
Br1 C4 H4A . . 108.7 ?
C3 C4 H4B . . 108.7 ?
Br1 C4 H4B . . 108.7 ?
H4A C4 H4B . . 107.6 ?
O1 C5 C3 . . 108.2(4) ?
O1 C5 H5A . . 110.1 ?
C3 C5 H5A . . 110.1 ?
O1 C5 H5B . . 110.1 ?
C3 C5 H5B . . 110.1 ?
H5A C5 H5B . . 108.4 ?
O1 C6 C11 . . 124.6(4) ?
O1 C6 C7 . . 116.1(4) ?
C11 C6 C7 . . 119.3(4) ?
C8 C7 C6 . . 120.8(4) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C7 C8 C9 . . 120.2(4) ?
C7 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
C8 C9 C10 . . 119.1(4) ?
C8 C9 C13 . . 121.5(4) ?
C10 C9 C13 . . 119.4(4) ?
C11 C10 C9 . . 121.0(4) ?
C11 C10 C12 . . 119.7(4) ?
C9 C10 C12 . . 119.2(4) ?
C10 C11 C6 . . 119.5(4) ?
C10 C11 H11 . . 120.2 ?
C6 C11 H11 . . 120.2 ?
N1 C12 C10 . . 179.1(6) ?
N2 C13 C9 . . 178.6(6) ?
C6 O1 C5 . . 117.4(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br2 C1 C3 C5 . . . . -178.0(3) ?
Br2 C1 C3 C2 . . . . -56.2(5) ?
Br2 C1 C3 C4 . . . . 61.0(5) ?
Br3 C2 C3 C5 . . . . 64.2(5) ?
Br3 C2 C3 C1 . . . . -53.4(5) ?
Br3 C2 C3 C4 . . . . -175.1(4) ?
C5 C3 C4 Br1 . . . . -56.9(5) ?
C1 C3 C4 Br1 . . . . 59.9(5) ?
C2 C3 C4 Br1 . . . . -177.7(3) ?
C1 C3 C5 O1 . . . . -176.3(4) ?
C2 C3 C5 O1 . . . . 61.1(5) ?
C4 C3 C5 O1 . . . . -55.1(5) ?
O1 C6 C7 C8 . . . . 179.1(5) ?
C11 C6 C7 C8 . . . . 0.0(7) ?
C6 C7 C8 C9 . . . . -0.3(8) ?
C7 C8 C9 C10 . . . . 0.9(7) ?
C7 C8 C9 C13 . . . . -178.1(5) ?
C8 C9 C10 C11 . . . . -1.1(7) ?
C13 C9 C10 C11 . . . . 177.9(5) ?
C8 C9 C10 C12 . . . . -179.9(5) ?
C13 C9 C10 C12 . . . . -0.9(7) ?
C9 C10 C11 C6 . . . . 0.8(7) ?
C12 C10 C11 C6 . . . . 179.5(4) ?
O1 C6 C11 C10 . . . . -179.3(4) ?
C7 C6 C11 C10 . . . . -0.2(7) ?
C11 C6 O1 C5 . . . . 1.1(7) ?
C7 C6 O1 C5 . . . . -178.0(4) ?
C3 C5 O1 C6 . . . . 177.3(4) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C11 H11 N1 2_666 0.93 2.47 3.385(7) 168.5 ?

####################################################################### 
# 
# 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_17gtu196_mct_10_0m
_database_code_depnum_ccdc_archive 'CCDC 1873484'
loop_
_audit_author_name
_audit_author_address
'Mustafa Can TASKAN, Ercan DUYGULU, Sevde DEMIR, Fatma YUKSEL'
;Gebze Technical University
Turkey
;
_audit_update_record             
;
2018-10-16 deposited with the CCDC.	2020-03-30 downloaded from the CCDC.
;
_audit_creation_date             2017-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 Br3 N2 O'
_chemical_formula_sum            'C13 H11 Br3 N2 O'
_chemical_formula_weight         450.97
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.678(3)
_cell_length_b                   29.054(10)
_cell_length_c                   7.724(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.503(5)
_cell_angle_gamma                90
_cell_volume                     1514.2(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6079
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   0.423
_shelx_estimated_absorpt_T_min   0.312
_exptl_absorpt_coefficient_mu    7.985
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   0.354
_exptl_transmission_factor_min   0.272
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8609
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.804
_diffrn_ambient_temperature      119.96
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2190
_reflns_number_total             2651
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.832
_refine_diff_density_min         -1.087
_refine_diff_density_rms         0.217
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2651
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0710
_refine_ls_restrained_S_all      1.178
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0159P)²+32.7901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1691
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.49320(16) 0.17316(4) 0.98058(15) 0.0256(3) Uani 1 1 d . . . . .
Br2 Br 0.02628(18) 0.18991(4) 0.24407(16) 0.0279(3) Uani 1 1 d . . . . .
Br3 Br -0.24085(18) 0.21073(4) 0.62289(18) 0.0286(3) Uani 1 1 d . . . . .
O1 O 0.1613(11) 0.0832(2) 0.7390(9) 0.0161(16) Uani 1 1 d . . . . .
N1 N 0.3042(15) -0.0794(4) 1.2134(13) 0.027(2) Uani 1 1 d . . . . .
N2 N 0.1785(14) 0.0550(4) 1.1705(13) 0.026(2) Uani 1 1 d . . . . .
C1 C 0.2901(15) -0.0601(4) 1.0816(15) 0.019(2) Uani 1 1 d . . . . .
C2 C 0.1979(14) 0.0360(4) 1.0503(13) 0.012(2) Uani 1 1 d . . . . .
C3 C 0.2246(14) 0.0133(4) 0.9008(14) 0.014(2) Uani 1 1 d . . . . .
C4 C 0.2109(14) 0.0392(4) 0.7397(14) 0.014(2) Uani 1 1 d . . . . .
C5 C 0.2481(14) 0.0185(4) 0.5992(14) 0.016(2) Uani 1 1 d . . . . .
H5 H 0.2401 0.0358 0.4913 0.019 Uiso 1 1 calc R . . . .
C6 C 0.2974(15) -0.0282(4) 0.6180(14) 0.018(2) Uani 1 1 d . . . . .
H6 H 0.3229 -0.0424 0.5215 0.022 Uiso 1 1 calc R . . . .
C7 C 0.3101(15) -0.0544(4) 0.7729(14) 0.019(2) Uani 1 1 d . . . . .
H7 H 0.3447 -0.0860 0.7831 0.022 Uiso 1 1 calc R . . . .
C8 C 0.2718(13) -0.0340(4) 0.9132(13) 0.013(2) Uani 1 1 d . . . . .
C9 C 0.1699(16) 0.1148(3) 0.6010(14) 0.016(2) Uani 1 1 d . . . . .
H9A H 0.0818 0.1044 0.4645 0.019 Uiso 1 1 calc R . . . .
H9B H 0.3069 0.1169 0.6208 0.019 Uiso 1 1 calc R . . . .
C10 C 0.1016(15) 0.1620(4) 0.6375(14) 0.016(2) Uani 1 1 d . . . . .
C11 C 0.2031(13) 0.1735(4) 0.8598(14) 0.018(2) Uani 1 1 d . . . . .
H11A H 0.1611 0.1508 0.9281 0.021 Uiso 1 1 calc R . . . .
H11B H 0.1586 0.2043 0.8777 0.021 Uiso 1 1 calc R . . . .
C12 C 0.1499(15) 0.1995(4) 0.5286(14) 0.020(2) Uani 1 1 d . . . . .
H12A H 0.2954 0.2010 0.5822 0.024 Uiso 1 1 calc R . . . .
H12B H 0.1058 0.2295 0.5543 0.024 Uiso 1 1 calc R . . . .
C13 C -0.1221(16) 0.1574(4) 0.5653(16) 0.023(3) Uani 1 1 d . . . . .
H13A H -0.1451 0.1299 0.6272 0.028 Uiso 1 1 calc R . . . .
H13B H -0.1903 0.1523 0.4211 0.028 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C11 1.962(9) . ?
Br2 C12 1.954(10) . ?
Br3 C13 1.954(11) . ?
O1 C4 1.334(13) . ?
O1 C9 1.431(12) . ?
N1 C1 1.121(14) . ?
N2 C2 1.149(13) . ?
C1 C8 1.454(14) . ?
C2 C3 1.428(14) . ?
C3 C4 1.415(14) . ?
C3 C8 1.411(15) . ?
C4 C5 1.385(14) . ?
C5 C6 1.397(15) . ?
C6 C7 1.381(15) . ?
C7 C8 1.384(14) . ?
C9 C10 1.540(15) . ?
C10 C11 1.546(13) . ?
C10 C12 1.527(14) . ?
C10 C13 1.538(15) . ?

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
C4 O1 C9 120.3(8) . . ?
N1 C1 C8 178.5(12) . . ?
N2 C2 C3 178.8(11) . . ?
C4 C3 C2 119.0(10) . . ?
C8 C3 C2 121.8(9) . . ?
C8 C3 C4 119.1(9) . . ?
O1 C4 C3 114.6(9) . . ?
O1 C4 C5 125.4(9) . . ?
C5 C4 C3 120.0(10) . . ?
C4 C5 C6 119.2(9) . . ?
C7 C6 C5 121.9(9) . . ?
C6 C7 C8 119.3(10) . . ?
C3 C8 C1 118.7(9) . . ?
C7 C8 C1 120.7(10) . . ?
C7 C8 C3 120.5(9) . . ?
O1 C9 C10 107.1(8) . . ?
C9 C10 C11 111.2(8) . . ?
C12 C10 C9 109.9(9) . . ?
C12 C10 C11 109.3(8) . . ?
C12 C10 C13 112.6(9) . . ?
C13 C10 C9 106.0(8) . . ?
C13 C10 C11 107.8(8) . . ?
C10 C11 Br1 112.5(7) . . ?
C10 C12 Br2 113.7(7) . . ?
C10 C13 Br3 114.3(7) . . ?

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 C4 C5 C6 -179.6(9) . . . . ?
O1 C9 C10 C11 46.3(11) . . . . ?
O1 C9 C10 C12 167.5(8) . . . . ?
O1 C9 C10 C13 -70.5(9) . . . . ?
C2 C3 C4 O1 -3.9(13) . . . . ?
C2 C3 C4 C5 176.1(9) . . . . ?
C2 C3 C8 C1 1.1(14) . . . . ?
C2 C3 C8 C7 -175.5(9) . . . . ?
C3 C4 C5 C6 0.5(14) . . . . ?
C4 O1 C9 C10 179.3(8) . . . . ?
C4 C3 C8 C1 178.5(9) . . . . ?
C4 C3 C8 C7 1.9(14) . . . . ?
C4 C5 C6 C7 0.1(15) . . . . ?
C5 C6 C7 C8 0.4(16) . . . . ?
C6 C7 C8 C1 -178.0(9) . . . . ?
C6 C7 C8 C3 -1.4(15) . . . . ?
C8 C3 C4 O1 178.6(8) . . . . ?
C8 C3 C4 C5 -1.5(14) . . . . ?
C9 O1 C4 C3 171.1(8) . . . . ?
C9 O1 C4 C5 -8.9(14) . . . . ?
C9 C10 C11 Br1 57.4(10) . . . . ?
C9 C10 C12 Br2 58.9(10) . . . . ?
C9 C10 C13 Br3 173.3(6) . . . . ?
C11 C10 C12 Br2 -178.8(7) . . . . ?
C11 C10 C13 Br3 54.2(10) . . . . ?
C12 C10 C11 Br1 -64.2(10) . . . . ?
C12 C10 C13 Br3 -66.4(10) . . . . ?
C13 C10 C11 Br1 173.1(7) . . . . ?
C13 C10 C12 Br2 -59.1(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
