# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1968851'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2019-11-28 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
###### original file name data_jil046_6
_audit_creation_date             2019-11-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 Br N O2'
_chemical_formula_sum            'C14 H10 Br N O2'
_chemical_formula_weight         304.14
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.7872(9)
_cell_length_b                   11.4491(7)
_cell_length_c                   7.3967(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.273(3)
_cell_angle_gamma                90
_cell_volume                     1145.05(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3627
_cell_measurement_temperature    100
_cell_measurement_theta_max      51.05
_cell_measurement_theta_min      5.06
_shelx_estimated_absorpt_T_max   0.794
_shelx_estimated_absorpt_T_min   0.445
_exptl_absorpt_coefficient_mu    4.837
_exptl_absorpt_correction_T_max  0.7503
_exptl_absorpt_correction_T_min  0.6205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0900 before and 0.0686 after correction. 
The Ratio of minimum to maximum transmission is 0.8270. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10189
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        51.851
_diffrn_reflns_theta_max         51.851
_diffrn_reflns_theta_min         3.268
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 Kappa Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       APEX2
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1130
_reflns_number_total             1274
_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       'SAINT v8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2017) '
_computing_data_reduction        'SAINT v8.37A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.935
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.165
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0957
_refine_ls_restrained_S_all      1.179
_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)+(0.0331P)²+33.4781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2070
_refine_ls_wR_factor_ref         0.2110
_refine_special_details          
;        
Poor diffraction characteristics with generally low intensity 
scattering and no useful reflections beyond 0.98 Angstrom. 
The bromine atom is partially occupied over two positions in a 
95:5 ratio, the occupancy of the second bromine is too low
to model onto any of the carbons associated with the correct geometry.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.31556(13) -0.09110(14) 0.4972(2) 0.0453(7) Uani 1 1 d . . . . .
O1 O 0.0566(7) 0.4188(9) 0.2623(13) 0.040(3) Uani 1 1 d . . . . .
N1 N 0.2033(9) 0.4985(11) 0.3862(17) 0.040(3) Uani 1 1 d . . . . .
C1 C 0.1169(12) 0.6655(14) 0.495(2) 0.046(4) Uani 1 1 d . . . . .
H1A H 0.083188 0.738909 0.453446 0.070 Uiso 1 1 calc GR . . . .
H1B H 0.168361 0.680150 0.604053 0.070 Uiso 1 1 calc GR . . . .
H1C H 0.068889 0.609475 0.525623 0.070 Uiso 1 1 calc GR . . . .
O2 O 0.3489(7) 0.5778(9) 0.5236(14) 0.042(3) Uani 1 1 d . . . . .
C2 C 0.1638(12) 0.6158(12) 0.342(2) 0.040(4) Uani 1 1 d . . . . .
H2A H 0.113691 0.612940 0.226018 0.048 Uiso 1 1 calc R . . . .
H2B H 0.217911 0.668007 0.321472 0.048 Uiso 1 1 calc R . . . .
C3 C 0.3028(10) 0.4911(13) 0.4835(18) 0.028(3) Uani 1 1 d . . . . .
C4 C 0.3444(10) 0.3707(13) 0.5240(19) 0.033(4) Uani 1 1 d . . . . .
C5 C 0.4383(12) 0.3597(13) 0.609(2) 0.039(4) Uani 1 1 d . . . . .
H5 H 0.477213 0.427861 0.641318 0.047 Uiso 1 1 calc R . . . .
C6 C 0.4807(11) 0.2506(15) 0.652(2) 0.043(4) Uani 1 1 d . . . . .
H6 H 0.547504 0.244844 0.715452 0.052 Uiso 1 1 calc R . . A .
C7 C 0.4271(10) 0.1525(15) 0.6038(19) 0.039(4) Uani 1 1 d . . . B 1
H7 H 0.456546 0.078099 0.633371 0.046 Uiso 1 1 calc R . . B 1
C8 C 0.3260(11) 0.1600(12) 0.5080(19) 0.029(3) Uani 1 1 d . . . . .
C9 C 0.2632(11) 0.0623(12) 0.456(2) 0.036(4) Uani 1 1 d . . . . .
C10 C 0.1667(10) 0.0745(13) 0.369(2) 0.036(4) Uani 1 1 d . . . . .
H10 H 0.126933 0.007420 0.333928 0.043 Uiso 1 1 calc R . . . .
C11 C 0.1268(11) 0.1863(13) 0.333(2) 0.035(4) Uani 1 1 d . . . . .
H11 H 0.059373 0.194863 0.274709 0.042 Uiso 1 1 calc R . . . .
C12 C 0.1854(11) 0.2857(12) 0.381(2) 0.033(4) Uani 1 1 d . . . . .
C13 C 0.1420(10) 0.4035(13) 0.3354(19) 0.033(4) Uani 1 1 d . . . . .
C14 C 0.2819(10) 0.2710(14) 0.4718(19) 0.036(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
C7a H7 0.9500 . ?
C7a C8 1.44(2) . ?
Br1 C9 1.901(14) . ?
O1 C13 1.208(16) . ?
N1 C2 1.462(18) . ?
N1 C3 1.423(18) . ?
N1 C13 1.383(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.52(2) . ?
O2 C3 1.184(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.50(2) . ?
C4 C5 1.33(2) . ?
C4 C14 1.44(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.39(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.35(2) . ?
C8 C9 1.42(2) . ?
C8 C14 1.41(2) . ?
C9 C10 1.37(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.40(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.401(19) . ?
C12 C13 1.49(2) . ?
C12 C14 1.38(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
C7a C6 C5 120.2(15) . . ?
C7a C6 H6 119.9 . . ?
C3 N1 C2 116.7(12) . . ?
C13 N1 C2 118.7(12) . . ?
C13 N1 C3 124.6(12) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 111.7(12) . . ?
N1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
N1 C3 C4 116.7(13) . . ?
O2 C3 N1 119.6(13) . . ?
O2 C3 C4 123.7(13) . . ?
C5 C4 C3 118.7(13) . . ?
C5 C4 C14 121.9(14) . . ?
C14 C4 C3 119.4(12) . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.3(15) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 119.9 . . ?
C9 C8 C7 124.5(14) . . ?
C14 C8 C7 119.2(14) . . ?
C14 C8 C9 116.2(13) . . ?
C8 C9 Br1 119.5(11) . . ?
C10 C9 Br1 118.3(12) . . ?
C10 C9 C8 122.1(13) . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(14) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(14) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 119.6(14) . . ?
C14 C12 C11 118.5(14) . . ?
C14 C12 C13 121.9(13) . . ?
O1 C13 N1 119.9(14) . . ?
O1 C13 C12 123.1(14) . . ?
N1 C13 C12 117.0(12) . . ?
C8 C14 C4 116.8(13) . . ?
C12 C14 C4 120.3(14) . . ?
C12 C14 C8 122.8(14) . . ?
C6 C7a H7 119.8 . . ?
C6 C7a C8 120.5(15) . . ?
C8 C7a H7 119.8 . . ?

_exptl.absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_THETM01_6                   
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..      51.85 Degree
RESPONSE:  Compound 6 exhibited poor diffraction characteristics with generally 
low intensity scattering and no useful reflections beyond 0.98 A resolution.
Only a low resolution dataset could be obtained.
;
####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1968853'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2019-11-28 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
_audit_creation_date             2017-10-31
_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         'C20 H22 Br N O2'
_chemical_formula_sum            'C20 H22 Br N O2'
_chemical_formula_weight         388.29
_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      triclinic
_space_group_IT_number           2
_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                   4.6972(2)
_cell_length_b                   11.9618(5)
_cell_length_c                   15.7954(7)
_cell_angle_alpha                81.534(3)
_cell_angle_beta                 86.654(4)
_cell_angle_gamma                84.890(3)
_cell_volume                     873.41(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2912
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.85
_cell_measurement_theta_min      3.75
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.655
_exptl_absorpt_coefficient_mu    3.296
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0825 before and 0.0554 after correction. The Ratio of minimum to maximum transmission is 0.6931. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7358
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.319
_diffrn_reflns_theta_min         3.748
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2664
_reflns_number_total             3139
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.239
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.140
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0732
_refine_ls_restrained_S_all      1.136
_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)+(0.1140P)²+0.9070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1867
_refine_ls_wR_factor_ref         0.1935
_refine_special_details          
;
Bromine atom at the naphthalimide 4-position is disordered over
two equivalent orientations ~93:07. The two bromine positions
were modelled, but the underlying 7% disorder of the carbon
skeleton could not be modelled without introducing redundant
parameters at no benefit to the structure model. As such, the 
bond lengths and angles involving Br2 are not especially 
reliable. Furthermore, the related packing disorder involving
Br2---C1 intermolecular contacts could not be resolved, 
due to the low occupancy of the second contributor, so 
C1 was modelled full occupancy PART 1 without locating the 
7% occupancy PART 2 contributor.
;
_olex2_refinement_description    
;
1. Others
 Fixed Sof: Br1(0.93) Br2(0.07) H13(0.07) H15(0.93)
 Fixed Uiso: H1A(0.081) H1B(0.081) H1C(0.081) H2A(0.055) H2B(0.055) H3A(0.05)
 H3B(0.05) H4A(0.048) H4B(0.048) H5A(0.046) H5B(0.046) H6A(0.045) H6B(0.045)
 H7A(0.041) H7B(0.041) H8A(0.036) H8B(0.036) H11(0.039) H12(0.042) H13(0.041)
 H15(0.04) H16(0.041) H17(0.038)
 Fixed X: H1A(1.0701) H1B(1.1872) H1C(0.8826) H2A(1.0007) H2B(0.6939)
 H3A(0.675) H3B(0.9841) H4A(0.4785) H4B(0.7882) H5A(0.8038) H5B(0.4899)
 H6A(0.5925) H6B(0.2869) H7A(0.4306) H7B(0.7026) H8A(0.3492) H8B(0.1175)
 H11(0.1265) H12(0.2409) H13(0.5477) H15(0.8681) H16(1.0587) H17(0.9447)
 Fixed Y: H1A(0.8801) H1B(0.8277) H1C(0.8992) H2A(0.6887) H2B(0.7582)
 H3A(0.724) H3B(0.6563) H4A(0.5818) H4B(0.5157) H5A(0.4825) H5B(0.5451)
 H6A(0.345) H6B(0.4011) H7A(0.2348) H7B(0.2945) H8A(0.4422) H8B(0.3522)
 H11(0.0201) H12(-0.0616) H13(0.0217) H15(0.1812) H16(0.3471) H17(0.4237)
 Fixed Z: H1A(-0.0491) H1B(0.0427) H1C(0.0363) H2A(-0.0276) H2B(-0.0252)
 H3A(0.127) H3B(0.1254) H4A(0.0652) H4B(0.0566) H5A(0.2096) H5B(0.2166)
 H6A(0.1376) H6B(0.1662) H7A(0.2627) H7B(0.2852) H8A(0.3337) H8B(0.3325)
 H11(0.5543) H12(0.6931) H13(0.7673) H15(0.7761) H16(0.7099) H17(0.5702)
;
_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 0.59455(15) -0.01335(5) 0.82412(4) 0.0421(3) Uani 0.93 1 d . . P A 1
Br2 Br 0.8491(19) 0.1230(8) 0.8358(6) 0.0480(19) Uani 0.07 1 d . . P B 2
O1 O 0.1070(7) 0.1671(3) 0.4196(2) 0.0342(8) Uani 1 1 d . . . . .
O2 O 0.7116(7) 0.4410(3) 0.4284(2) 0.0335(8) Uani 1 1 d . . . . .
N1 N 0.3997(8) 0.3065(3) 0.4255(3) 0.0287(8) Uani 1 1 d . . . . .
C1 C 1.0157(16) 0.8458(6) 0.0092(4) 0.0538(15) Uani 1 1 d . . . C 1
H1A H 1.0701 0.8801 -0.0491 0.081 Uiso 1 1 calc GR . . C 1
H1B H 1.1872 0.8277 0.0427 0.081 Uiso 1 1 calc GR . . C 1
H1C H 0.8826 0.8992 0.0363 0.081 Uiso 1 1 calc GR . . C 1
C2 C 0.8734(14) 0.7387(5) 0.0055(4) 0.0461(13) Uani 1 1 d . . . . .
H2A H 1.0007 0.6887 -0.0276 0.055 Uiso 1 1 calc R . . C .
H2B H 0.6939 0.7582 -0.0252 0.055 Uiso 1 1 calc R . . C .
C3 C 0.8048(13) 0.6742(5) 0.0944(4) 0.0417(12) Uani 1 1 d . . . . .
H3A H 0.6750 0.7240 0.1270 0.050 Uiso 1 1 calc R . . . .
H3B H 0.9841 0.6563 0.1254 0.050 Uiso 1 1 calc R . . . .
C4 C 0.6650(12) 0.5638(5) 0.0923(4) 0.0402(12) Uani 1 1 d . . . . .
H4A H 0.4785 0.5818 0.0652 0.048 Uiso 1 1 calc R . . . .
H4B H 0.7882 0.5157 0.0566 0.048 Uiso 1 1 calc R . . . .
C5 C 0.6179(12) 0.4975(5) 0.1818(3) 0.0384(11) Uani 1 1 d . . . . .
H5A H 0.8038 0.4825 0.2096 0.046 Uiso 1 1 calc R . . . .
H5B H 0.4899 0.5451 0.2166 0.046 Uiso 1 1 calc R . . . .
C6 C 0.4890(12) 0.3856(5) 0.1819(3) 0.0376(11) Uani 1 1 d . . . . .
H6A H 0.5925 0.3450 0.1376 0.045 Uiso 1 1 calc R . . . .
H6B H 0.2869 0.4011 0.1662 0.045 Uiso 1 1 calc R . . . .
C7 C 0.5011(11) 0.3087(4) 0.2686(3) 0.0342(11) Uani 1 1 d . . . . .
H7A H 0.4306 0.2348 0.2627 0.041 Uiso 1 1 calc R . . . .
H7B H 0.7026 0.2945 0.2852 0.041 Uiso 1 1 calc R . . . .
C8 C 0.3225(10) 0.3602(4) 0.3396(3) 0.0297(10) Uani 1 1 d . . . . .
H8A H 0.3492 0.4422 0.3337 0.036 Uiso 1 1 calc R . . . .
H8B H 0.1175 0.3522 0.3325 0.036 Uiso 1 1 calc R . . . .
C9 C 0.2764(9) 0.2062(4) 0.4604(3) 0.0280(10) Uani 1 1 d . . . . .
C10 C 0.3618(10) 0.1544(4) 0.5466(3) 0.0281(9) Uani 1 1 d . . . . .
C11 C 0.2522(11) 0.0557(4) 0.5849(3) 0.0327(10) Uani 1 1 d . . . . .
H11 H 0.1265 0.0201 0.5543 0.039 Uiso 1 1 calc R . . . .
C12 C 0.3207(10) 0.0063(4) 0.6676(4) 0.0347(11) Uani 1 1 d . . . . .
H12 H 0.2409 -0.0616 0.6931 0.042 Uiso 1 1 calc R . . . .
C13 C 0.5022(11) 0.0563(4) 0.7111(3) 0.0345(11) Uani 1 1 d . . . . .
H13 H 0.5477 0.0217 0.7673 0.041 Uiso 0.07 1 calc R . P A 2
C14 C 0.6279(10) 0.1581(4) 0.6765(3) 0.0313(10) Uani 1 1 d . . . . .
C15 C 0.8178(10) 0.2123(4) 0.7196(3) 0.0330(10) Uani 1 1 d . . . . .
H15 H 0.8681 0.1812 0.7761 0.040 Uiso 0.93 1 calc R . P B 1
C16 C 0.9320(10) 0.3108(4) 0.6801(4) 0.0339(11) Uani 1 1 d . . . . .
H16 H 1.0587 0.3471 0.7099 0.041 Uiso 1 1 calc R . . . .
C17 C 0.8624(10) 0.3570(4) 0.5971(3) 0.0317(10) Uani 1 1 d . . . . .
H17 H 0.9447 0.4237 0.5702 0.038 Uiso 1 1 calc R . . . .
C18 C 0.6747(9) 0.3065(4) 0.5533(3) 0.0287(10) Uani 1 1 d . . . . .
C19 C 0.6048(10) 0.3568(4) 0.4660(3) 0.0282(9) Uani 1 1 d . . . . .
C20 C 0.5549(10) 0.2055(4) 0.5923(3) 0.0287(10) 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
Br1 C13 1.912(5) . ?
Br2 C15 1.990(11) . ?
O1 C9 1.217(6) . ?
O2 C19 1.223(6) . ?
N1 C8 1.465(6) . ?
N1 C9 1.404(6) . ?
N1 C19 1.409(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.507(9) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.531(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.531(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.531(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.517(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.535(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.530(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.472(7) . ?
C10 C11 1.374(7) . ?
C10 C20 1.423(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.395(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.356(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.423(7) . ?
C14 C15 1.408(7) . ?
C14 C20 1.416(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(8) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(7) . ?
C18 C19 1.465(7) . ?
C18 C20 1.420(7) . ?

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
C9 N1 C8 118.4(4) . . ?
C9 N1 C19 124.3(4) . . ?
C19 N1 C8 117.2(4) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C1 C2 C3 112.8(5) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C2 C3 C4 113.8(5) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 C3 112.4(5) . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 C4 113.8(5) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C5 C6 C7 113.4(4) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 112.6(4) . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
N1 C8 C7 112.6(4) . . ?
N1 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
O1 C9 N1 119.7(5) . . ?
O1 C9 C10 123.7(4) . . ?
N1 C9 C10 116.6(4) . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 C20 118.6(5) . . ?
C20 C10 C9 121.2(4) . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.8(5) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.3(5) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 Br1 118.5(4) . . ?
C12 C13 H13 118.5 . . ?
C12 C13 C14 123.0(5) . . ?
C14 C13 Br1 118.5(4) . . ?
C14 C13 H13 118.5 . . ?
C15 C14 C13 124.7(5) . . ?
C15 C14 C20 119.1(5) . . ?
C20 C14 C13 116.2(4) . . ?
C14 C15 Br2 106.2(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 Br2 133.3(5) . . ?
C16 C15 C14 120.5(5) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(5) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.5(5) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 119.5(4) . . ?
C17 C18 C20 120.1(5) . . ?
C20 C18 C19 120.4(4) . . ?
O2 C19 N1 119.6(5) . . ?
O2 C19 C18 122.7(4) . . ?
N1 C19 C18 117.6(4) . . ?
C14 C20 C10 121.2(4) . . ?
C14 C20 C18 119.3(4) . . ?
C18 C20 C10 119.6(5) . . ?

_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_7
_database_code_depnum_ccdc_archive 'CCDC 1968852'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2019-11-28 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;

###### original file name data_cu_jil050_0m
_audit_creation_date             2019-11-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C16 H14 Br N O2)'
_chemical_formula_sum            'C32 H28 Br2 N2 O4'
_chemical_formula_weight         664.38
_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      triclinic
_space_group_IT_number           2
_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                   4.4247(3)
_cell_length_b                   16.1174(10)
_cell_length_c                   19.4957(13)
_cell_angle_alpha                99.692(2)
_cell_angle_beta                 94.484(2)
_cell_angle_gamma                92.775(2)
_cell_volume                     1363.61(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9604
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.525
_exptl_absorpt_coefficient_mu    4.115
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;  
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0681 before and 0.0440 after correction. 
The Ratio of minimum to maximum transmission is 0.7776. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12740
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.213
_diffrn_reflns_theta_min         2.787
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4759
_reflns_number_total             4955
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.959
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         4955
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.167
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+2.6902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1066
_refine_special_details          
;       
C25 exhibits an unusual geometry due to the partially occupied
bromine atom (modelled as Br2 and Br3) in a 93:7 ratio. 
The occupancy of 0.07 for Br3 is too low to model onto any of 
the carbons associated with the correct geometry.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C27-Br2
 1.9 with sigma of 0.01
 C25-Br3
 1.9 with sigma of 0.01
3. Others
 Fixed Sof: Br2(0.93172) Br3(0.07071) H25(0.93) H27(0.06828)
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C18(H18A,H18B), C19(H19A,H19B),
 C20(H20A,H20B)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C23(H23), C24(H24), C27(H27),
 C28(H28), C29(H29)
4.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.11369(8) 0.39982(2) 0.48556(2) 0.03191(12) Uani 1 1 d . . . A 2
O1 O -0.1103(5) -0.07949(13) 0.36818(11) 0.0284(5) Uani 1 1 d . . . . .
N1 N 0.2097(6) -0.00764(15) 0.30956(13) 0.0219(5) Uani 1 1 d . . . . .
C1 C 0.0434(10) -0.1896(3) 0.0718(2) 0.0477(10) Uani 1 1 d . . . . .
H1A H -0.177260 -0.186041 0.071121 0.071 Uiso 1 1 calc GR . . . .
H1B H 0.089544 -0.244409 0.046014 0.071 Uiso 1 1 calc GR . . . .
H1C H 0.130040 -0.144466 0.049940 0.071 Uiso 1 1 calc GR . . . .
O2 O 0.5384(5) 0.06505(14) 0.25438(11) 0.0285(5) Uani 1 1 d . . . . .
C2 C 0.1800(8) -0.1799(2) 0.14707(18) 0.0336(7) Uani 1 1 d . . . . .
H2A H 0.401931 -0.185427 0.147360 0.040 Uiso 1 1 calc R . . . .
H2B H 0.093140 -0.225894 0.168737 0.040 Uiso 1 1 calc R . . . .
C3 C 0.1210(7) -0.0953(2) 0.19063(16) 0.0277(6) Uani 1 1 d . . . . .
H3A H 0.199467 -0.048888 0.168143 0.033 Uiso 1 1 calc R . . . .
H3B H -0.100442 -0.090657 0.192833 0.033 Uiso 1 1 calc R . . . .
C4 C 0.2751(7) -0.08669(19) 0.26432(16) 0.0267(6) Uani 1 1 d . . . . .
H4A H 0.205561 -0.135219 0.285403 0.032 Uiso 1 1 calc R . . . .
H4B H 0.497405 -0.088450 0.261887 0.032 Uiso 1 1 calc R . . . .
C5 C 0.3555(6) 0.06691(19) 0.29792(15) 0.0223(6) Uani 1 1 d . . . . .
C6 C 0.2809(6) 0.14668(18) 0.34136(15) 0.0209(6) Uani 1 1 d . . . . .
C7 C 0.4067(7) 0.2222(2) 0.33000(16) 0.0246(6) Uani 1 1 d . . . . .
H7 H 0.533228 0.223209 0.292923 0.029 Uiso 1 1 calc R . . . .
C8 C 0.3497(7) 0.29811(19) 0.37276(16) 0.0248(6) Uani 1 1 d . . . . .
H8 H 0.434037 0.350385 0.364277 0.030 Uiso 1 1 calc R . . . .
C9 C 0.1713(7) 0.29588(19) 0.42684(15) 0.0241(6) Uani 1 1 d . . . . .
C10 C 0.0327(6) 0.22028(19) 0.44096(15) 0.0216(6) Uani 1 1 d . . . . .
C11 C -0.1562(7) 0.2149(2) 0.49599(15) 0.0258(6) Uani 1 1 d . . . . .
H11 H -0.196692 0.264800 0.526495 0.031 Uiso 1 1 calc R . . . .
C12 C -0.2800(7) 0.1390(2) 0.50549(16) 0.0274(6) Uani 1 1 d . . . . .
H12 H -0.405373 0.136467 0.542575 0.033 Uiso 1 1 calc R . . . .
C13 C -0.2236(7) 0.0645(2) 0.46092(16) 0.0252(6) Uani 1 1 d . . . . .
H13 H -0.311268 0.011923 0.467933 0.030 Uiso 1 1 calc R . . . .
C14 C -0.0420(6) 0.06729(18) 0.40714(15) 0.0214(6) Uani 1 1 d . . . . .
C15 C 0.0111(7) -0.01264(19) 0.36101(15) 0.0226(6) Uani 1 1 d . . . . .
C16 C 0.0902(6) 0.14493(18) 0.39604(14) 0.0202(6) Uani 1 1 d . . . . .
Br2 Br 1.69285(9) 0.72888(2) 0.33076(2) 0.03453(12) Uani 0.9317 1 d D . P B -2
N2 N 0.8301(6) 0.37498(16) 0.15612(13) 0.0231(5) Uani 1 1 d . . . . .
Br3 Br 1.7740(13) 0.7300(3) 0.2554(4) 0.0560(17) Uani 0.0707 1 d D . P C -1
O3 O 0.7586(6) 0.36615(15) 0.26917(13) 0.0367(6) Uani 1 1 d . . . . .
H25 H 1.695(8) 0.686(3) 0.1874(19) 0.023(9) Uiso 0.93 1 d . . P D 1
O4 O 0.9148(6) 0.38173(15) 0.04395(11) 0.0335(5) Uani 1 1 d . . . . .
C17 C 0.7255(8) 0.0593(2) 0.08954(19) 0.0336(7) Uani 1 1 d . . . . .
H17A H 0.879528 0.061442 0.056277 0.050 Uiso 1 1 calc GR . . . .
H17B H 0.576742 0.012057 0.071788 0.050 Uiso 1 1 calc GR . . . .
H17C H 0.823429 0.051570 0.134685 0.050 Uiso 1 1 calc GR . . . .
C18 C 0.5649(7) 0.1417(2) 0.09869(18) 0.0289(7) Uani 1 1 d . . . . .
H18A H 0.459760 0.148012 0.053327 0.035 Uiso 1 1 calc R . . . .
H18B H 0.409192 0.139034 0.132192 0.035 Uiso 1 1 calc R . . . .
C19 C 0.7836(7) 0.21859(19) 0.12509(17) 0.0257(6) Uani 1 1 d . . . . .
H19A H 0.885378 0.213068 0.171019 0.031 Uiso 1 1 calc R . . . .
H19B H 0.941906 0.220765 0.092147 0.031 Uiso 1 1 calc R . . . .
C20 C 0.6200(7) 0.30039(19) 0.13242(18) 0.0279(7) Uani 1 1 d . . . . .
H20A H 0.513741 0.305074 0.086751 0.033 Uiso 1 1 calc R . . . .
H20B H 0.465211 0.298708 0.166250 0.033 Uiso 1 1 calc R . . . .
C21 C 0.9682(7) 0.41191(19) 0.10578(15) 0.0232(6) Uani 1 1 d . . . . .
C22 C 1.1769(7) 0.48742(19) 0.13063(16) 0.0229(6) Uani 1 1 d . . . . .
C23 C 1.3121(7) 0.5262(2) 0.08222(17) 0.0293(7) Uani 1 1 d . . . . .
H23 H 1.273739 0.503660 0.033887 0.035 Uiso 1 1 calc R . . . .
C24 C 1.5062(8) 0.5987(2) 0.10376(19) 0.0343(7) Uani 1 1 d . . . . .
H24 H 1.600006 0.624678 0.069886 0.041 Uiso 1 1 calc R . . . .
C25 C 1.5628(7) 0.6330(2) 0.17391(19) 0.0330(7) Uani 1 1 d D . . . .
C26 C 1.4235(7) 0.5940(2) 0.22496(18) 0.0284(7) Uani 1 1 d . . . . .
C27 C 1.4631(7) 0.62510(19) 0.29741(18) 0.0314(7) Uani 1 1 d D . . . .
H27 H 1.584037 0.675951 0.313799 0.038 Uiso 0.0683 1 calc R . P B 1
C28 C 1.3341(8) 0.5846(2) 0.34422(17) 0.0345(8) Uani 1 1 d . . . . .
H28 H 1.372619 0.606130 0.392739 0.041 Uiso 1 1 calc R . . . .
C29 C 1.1424(8) 0.5106(2) 0.32169(17) 0.0321(7) Uani 1 1 d . . . . .
H29 H 1.050716 0.483206 0.355013 0.039 Uiso 1 1 calc R . . . .
C30 C 1.0887(7) 0.47847(19) 0.25183(16) 0.0242(6) Uani 1 1 d . . . . .
C31 C 0.8816(7) 0.40304(19) 0.22797(16) 0.0259(6) Uani 1 1 d . . . . .
C32 C 1.2305(7) 0.51951(18) 0.20258(16) 0.0227(6) 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
BR1b C9 1.903(3) . ?
O1 C15 1.215(4) . ?
N1 C4 1.477(4) . ?
N1 C5 1.397(4) . ?
N1 C15 1.394(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.522(5) . ?
O2 C5 1.216(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.526(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.523(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.482(4) . ?
C6 C7 1.373(4) . ?
C6 C16 1.413(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.405(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.370(4) . ?
C9 C10 1.415(4) . ?
C10 C11 1.422(4) . ?
C10 C16 1.419(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.363(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.404(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.375(4) . ?
C14 C15 1.482(4) . ?
C14 C16 1.412(4) . ?
Br2 C27 1.902(3) . ?
N2 C20 1.470(4) . ?
N2 C21 1.395(4) . ?
N2 C31 1.395(4) . ?
Br3 C25 2.153(6) . ?
O3 C31 1.222(4) . ?
O4 C21 1.222(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 C18 1.526(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.526(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.526(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.480(4) . ?
C22 C23 1.375(4) . ?
C22 C32 1.408(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.400(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.384(5) . ?
C25 H25 0.99(4) . ?
C25 C26 1.426(5) . ?
C26 C27 1.411(5) . ?
C26 C32 1.424(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.353(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.415(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.371(4) . ?
C30 C31 1.473(5) . ?
C30 C32 1.422(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C4 117.1(2) . . ?
C15 N1 C4 118.1(2) . . ?
C15 N1 C5 124.8(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C1 C2 C3 112.6(3) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 C2 110.7(3) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
N1 C4 C3 112.5(2) . . ?
N1 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N1 C5 C6 117.2(3) . . ?
O2 C5 N1 120.5(3) . . ?
O2 C5 C6 122.3(3) . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 C16 120.0(3) . . ?
C16 C6 C5 120.2(3) . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.5(3) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 Br1 117.7(2) . . ?
C8 C9 C10 123.0(3) . . ?
C10 C9 Br1 119.3(2) . . ?
C9 C10 C11 125.0(3) . . ?
C9 C10 C16 116.3(3) . . ?
C16 C10 C11 118.6(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 118.7(3) . . ?
C13 C14 C16 120.6(3) . . ?
C16 C14 C15 120.7(3) . . ?
O1 C15 N1 121.6(3) . . ?
O1 C15 C14 121.5(3) . . ?
N1 C15 C14 116.9(3) . . ?
C6 C16 C10 120.9(3) . . ?
C14 C16 C6 119.9(3) . . ?
C14 C16 C10 119.2(3) . . ?
C21 N2 C20 118.2(3) . . ?
C31 N2 C20 117.3(3) . . ?
C31 N2 C21 124.5(3) . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
C17 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 C17 112.6(3) . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C18 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 C18 111.8(2) . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
N2 C20 C19 112.2(2) . . ?
N2 C20 H20A 109.2 . . ?
N2 C20 H20B 109.2 . . ?
C19 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
N2 C21 C22 117.4(3) . . ?
O4 C21 N2 119.9(3) . . ?
O4 C21 C22 122.7(3) . . ?
C23 C22 C21 118.8(3) . . ?
C23 C22 C32 120.9(3) . . ?
C32 C22 C21 120.3(3) . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.7(3) . . ?
C25 C24 H24 119.7 . . ?
Br3 C25 H25 32(2) . . ?
C24 C25 Br3 150.3(3) . . ?
C24 C25 H25 119(2) . . ?
C24 C25 C26 119.9(3) . . ?
C26 C25 Br3 89.8(3) . . ?
C26 C25 H25 121(2) . . ?
C27 C26 C25 123.9(3) . . ?
C27 C26 C32 117.1(3) . . ?
C32 C26 C25 119.0(3) . . ?
C26 C27 Br2 119.5(3) . . ?
C26 C27 H27 119.0 . . ?
C28 C27 Br2 118.5(3) . . ?
C28 C27 C26 121.9(3) . . ?
C28 C27 H27 119.0 . . ?
C27 C28 H28 119.6 . . ?
C27 C28 C29 120.7(3) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.1(3) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C31 120.3(3) . . ?
C29 C30 C32 119.4(3) . . ?
C32 C30 C31 120.3(3) . . ?
N2 C31 C30 117.4(3) . . ?
O3 C31 N2 120.9(3) . . ?
O3 C31 C30 121.7(3) . . ?
C22 C32 C26 119.2(3) . . ?
C22 C32 C30 120.1(3) . . ?
C30 C32 C26 120.8(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
