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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_y-3-37
_database_code_depnum_ccdc_archive 'CCDC 1952777'
loop_
_audit_author_name
_audit_author_address
'Yan-Biao Kang'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2019-09-11 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;
_audit_creation_date             2019-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H8 Cl N O'
_chemical_formula_sum            'C14 H8 Cl N O'
_chemical_formula_weight         241.66
_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 0.0181 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'
Cl Cl 0.3639 0.7018 '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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.7356(3)
_cell_length_b                   5.75805(13)
_cell_length_c                   24.9630(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2118.07(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3319
_cell_measurement_temperature    291(2)
_cell_measurement_theta_min      6.0140
_cell_measurement_theta_max      73.8480
_shelx_estimated_absorpt_T_max   0.584
_shelx_estimated_absorpt_T_min   0.544
_exptl_absorpt_coefficient_mu    3.014
_exptl_absorpt_correction_T_min  0.49394
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            4814
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.578
_diffrn_reflns_theta_min         3.541
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1944
_reflns_number_total             2073
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2073
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+0.6299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1019
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C6(H6), C14(H14), C12(H12), C13(H13), C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.66872(3) -0.19185(8) 0.49426(2) 0.05202(18) Uani 1 1 d . . . . .
O1 O 0.67348(7) -0.05669(19) 0.73678(4) 0.0369(3) Uani 1 1 d . . . . .
N1 N 0.57331(8) 0.4169(2) 0.67373(5) 0.0358(3) Uani 1 1 d . . . . .
H1 H 0.5472 0.5502 0.6759 0.043 Uiso 1 1 calc R . . . .
C8 C 0.60548(9) 0.2870(3) 0.71573(6) 0.0323(3) Uani 1 1 d . . . . .
C10 C 0.65166(9) 0.0619(3) 0.78335(6) 0.0332(3) Uani 1 1 d . . . . .
C11 C 0.66894(10) -0.0180(3) 0.83442(6) 0.0382(4) Uani 1 1 d . . . . .
H11 H 0.6977 -0.1594 0.8403 0.046 Uiso 1 1 calc R . . . .
C6 C 0.66096(10) -0.0714(3) 0.59864(6) 0.0351(3) Uani 1 1 d . . . . .
H6 H 0.6914 -0.2093 0.6058 0.042 Uiso 1 1 calc R . . . .
C14 C 0.58180(10) 0.4144(3) 0.81629(6) 0.0362(3) Uani 1 1 d . . . . .
H14 H 0.5533 0.5565 0.8107 0.043 Uiso 1 1 calc R . . . .
C4 C 0.59064(9) 0.2934(3) 0.62720(6) 0.0340(3) Uani 1 1 d . . . . .
C12 C 0.64136(11) 0.1225(3) 0.87655(6) 0.0413(4) Uani 1 1 d . . . . .
H12 H 0.6519 0.0742 0.9115 0.050 Uiso 1 1 calc R . . . .
C7 C 0.64355(9) 0.0887(3) 0.69660(6) 0.0328(3) Uani 1 1 d . . . . .
C1 C 0.63833(10) -0.0095(3) 0.54702(6) 0.0383(3) Uani 1 1 d . . . . .
C13 C 0.59816(11) 0.3348(3) 0.86762(6) 0.0414(4) Uani 1 1 d . . . . .
H13 H 0.5801 0.4242 0.8967 0.050 Uiso 1 1 calc R . . . .
C5 C 0.63638(9) 0.0813(3) 0.63989(6) 0.0317(3) Uani 1 1 d . . . . .
C9 C 0.60893(9) 0.2771(3) 0.77309(6) 0.0312(3) Uani 1 1 d . . . . .
C2 C 0.59272(11) 0.1963(3) 0.53479(6) 0.0434(4) Uani 1 1 d . . . . .
H2 H 0.5782 0.2301 0.4994 0.052 Uiso 1 1 calc R . . . .
C3 C 0.56914(11) 0.3494(3) 0.57465(6) 0.0416(4) Uani 1 1 d . . . . .
H3 H 0.5394 0.4875 0.5666 0.050 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
Cl1 C1 1.7430(16) . ?
O1 C10 1.3862(18) . ?
O1 C7 1.3789(18) . ?
N1 C8 1.3725(19) . ?
N1 C4 1.3854(19) . ?
C8 C7 1.359(2) . ?
C8 C9 1.434(2) . ?
C10 C11 1.379(2) . ?
C10 C9 1.413(2) . ?
C11 C12 1.388(2) . ?
C6 C1 1.378(2) . ?
C6 C5 1.402(2) . ?
C14 C13 1.382(2) . ?
C14 C9 1.396(2) . ?
C4 C5 1.430(2) . ?
C4 C3 1.387(2) . ?
C12 C13 1.396(2) . ?
C7 C5 1.420(2) . ?
C1 C2 1.396(2) . ?
C2 C3 1.374(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C10 103.69(11) . . ?
C8 N1 C4 107.28(12) . . ?
N1 C8 C9 142.81(14) . . ?
C7 C8 N1 109.40(13) . . ?
C7 C8 C9 107.65(13) . . ?
O1 C10 C9 112.54(12) . . ?
C11 C10 O1 124.61(14) . . ?
C11 C10 C9 122.85(14) . . ?
C10 C11 C12 116.87(15) . . ?
C1 C6 C5 117.53(14) . . ?
C13 C14 C9 118.59(14) . . ?
N1 C4 C5 109.84(13) . . ?
N1 C4 C3 129.15(14) . . ?
C3 C4 C5 121.00(14) . . ?
C11 C12 C13 121.53(15) . . ?
O1 C7 C5 136.95(13) . . ?
C8 C7 O1 112.74(13) . . ?
C8 C7 C5 110.16(13) . . ?
C6 C1 Cl1 119.25(13) . . ?
C6 C1 C2 122.72(15) . . ?
C2 C1 Cl1 118.02(12) . . ?
C14 C13 C12 121.21(15) . . ?
C6 C5 C4 119.66(13) . . ?
C6 C5 C7 137.03(14) . . ?
C7 C5 C4 103.31(13) . . ?
C10 C9 C8 103.38(13) . . ?
C14 C9 C8 137.65(14) . . ?
C14 C9 C10 118.96(13) . . ?
C3 C2 C1 120.52(15) . . ?
C2 C3 C4 118.56(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_y-3-4-1
_database_code_depnum_ccdc_archive 'CCDC 1952778'
loop_
_audit_author_name
_audit_author_address
'Yan-Biao Kang'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2019-09-11 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;
_audit_creation_date             2019-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H8 Br N O'
_chemical_formula_sum            'C14 H8 Br N O'
_chemical_formula_weight         286.12
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 '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'

_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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
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                   8.28779(11)
_cell_length_b                   5.59996(10)
_cell_length_c                   24.2843(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1127.07(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7946
_cell_measurement_temperature    291(2)
_cell_measurement_theta_min      5.4350
_cell_measurement_theta_max      73.6760
_shelx_estimated_absorpt_T_max   0.495
_shelx_estimated_absorpt_T_min   0.447
_exptl_absorpt_coefficient_mu    4.806
_exptl_absorpt_correction_T_min  0.17127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9432
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.781
_diffrn_reflns_theta_min         3.640
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                2201
_reflns_number_total             2233
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1036 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       0.0039(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2233
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.044
_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)+(0.0559P)²+0.2593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0833
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C2(H2), N1(H1), C3(H3), C6(H6), C10(H10), C13(H13), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.34174(6) 0.87852(10) 0.49856(2) 0.0685(2) Uani 1 1 d . . . . .
O1 O 0.6275(3) 0.9769(5) 0.30614(12) 0.0389(5) Uani 1 1 d . . . . .
C11 C 0.8488(4) 0.9245(8) 0.1241(2) 0.0461(9) Uani 1 1 d . . . . .
H11 H 0.9172 1.0231 0.1040 0.055 Uiso 1 1 calc R . . . .
C4 C 0.4757(4) 0.6345(6) 0.32107(15) 0.0348(7) Uani 1 1 d . . . . .
C2 C 0.3413(5) 0.5631(9) 0.4068(2) 0.0475(9) Uani 1 1 d . . . . .
H2 H 0.2762 0.4690 0.4292 0.057 Uiso 1 1 calc R . . . .
N1 N 0.5520(4) 0.4956(5) 0.21927(13) 0.0366(6) Uani 1 1 d . . . . .
H1 H 0.5069 0.3595 0.2136 0.044 Uiso 1 1 calc R . . . .
C5 C 0.5321(4) 0.8516(6) 0.34289(15) 0.0367(7) Uani 1 1 d . . . . .
C14 C 0.6474(4) 0.6207(6) 0.18244(18) 0.0350(8) Uani 1 1 d . . . . .
C3 C 0.3792(5) 0.4884(7) 0.35394(17) 0.0421(8) Uani 1 1 d . . . . .
H3 H 0.3409 0.3434 0.3406 0.051 Uiso 1 1 calc R . . . .
C7 C 0.5430(4) 0.6297(5) 0.26672(15) 0.0348(7) Uani 1 1 d . . . . .
C9 C 0.7025(4) 0.8373(6) 0.20688(15) 0.0334(7) Uani 1 1 d . . . . .
C6 C 0.4978(5) 0.9285(7) 0.39589(17) 0.0430(8) Uani 1 1 d . . . . .
H6 H 0.5376 1.0712 0.4100 0.052 Uiso 1 1 calc R . . . .
C10 C 0.8038(4) 0.9904(7) 0.17691(16) 0.0383(7) Uani 1 1 d . . . . .
H10 H 0.8399 1.1330 0.1922 0.046 Uiso 1 1 calc R . . . .
C13 C 0.6919(5) 0.5583(7) 0.12894(17) 0.0415(8) Uani 1 1 d . . . . .
H13 H 0.6551 0.4180 0.1128 0.050 Uiso 1 1 calc R . . . .
C8 C 0.6310(4) 0.8330(6) 0.26024(15) 0.0342(7) Uani 1 1 d . . . . .
C1 C 0.4007(5) 0.7781(8) 0.42609(15) 0.0460(8) Uani 1 1 d . . . . .
C12 C 0.7932(5) 0.7133(8) 0.10068(16) 0.0462(8) Uani 1 1 d . . . . .
H12 H 0.8249 0.6747 0.0650 0.055 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 C1 1.911(4) . ?
O1 C5 1.384(5) . ?
O1 C8 1.376(5) . ?
C11 C10 1.385(6) . ?
C11 C12 1.391(7) . ?
C4 C5 1.406(5) . ?
C4 C3 1.395(5) . ?
C4 C7 1.433(5) . ?
C2 C3 1.385(7) . ?
C2 C1 1.383(7) . ?
N1 C14 1.384(5) . ?
N1 C7 1.377(5) . ?
C5 C6 1.387(5) . ?
C14 C9 1.426(5) . ?
C14 C13 1.395(6) . ?
C7 C8 1.362(5) . ?
C9 C10 1.403(5) . ?
C9 C8 1.425(5) . ?
C6 C1 1.376(6) . ?
C13 C12 1.389(6) . ?

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
C8 O1 C5 103.8(3) . . ?
C10 C11 C12 121.1(4) . . ?
C5 C4 C7 103.5(3) . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 C7 137.7(3) . . ?
C1 C2 C3 119.8(4) . . ?
C7 N1 C14 107.2(3) . . ?
O1 C5 C4 112.7(3) . . ?
O1 C5 C6 123.9(3) . . ?
C6 C5 C4 123.4(4) . . ?
N1 C14 C9 110.2(3) . . ?
N1 C14 C13 128.8(3) . . ?
C13 C14 C9 121.1(4) . . ?
C2 C3 C4 118.9(4) . . ?
N1 C7 C4 143.3(3) . . ?
C8 C7 C4 107.4(3) . . ?
C8 C7 N1 109.3(3) . . ?
C10 C9 C14 119.7(3) . . ?
C10 C9 C8 136.9(3) . . ?
C8 C9 C14 103.4(3) . . ?
C1 C6 C5 115.1(4) . . ?
C11 C10 C9 118.6(3) . . ?
C12 C13 C14 117.6(4) . . ?
O1 C8 C9 137.4(3) . . ?
C7 C8 O1 112.6(3) . . ?
C7 C8 C9 110.0(3) . . ?
C2 C1 Br1 118.5(3) . . ?
C6 C1 Br1 117.4(3) . . ?
C6 C1 C2 124.1(4) . . ?
C13 C12 C11 121.9(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
