# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_3e
_database_code_depnum_ccdc_archive 'CCDC 1847720'
_audit_update_record             
;
2018-08-12 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 N2 O4'
_chemical_formula_weight         308.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.457(8)
_cell_length_b                   7.977(4)
_cell_length_c                   25.613(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.424(9)
_cell_angle_gamma                90
_cell_volume                     2935(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7169
_cell_measurement_theta_min      2.5533
_cell_measurement_theta_max      27.5165

_exptl_crystal_description       Bloc
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27086
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.648
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6713
_reflns_number_gt                3732
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1249P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6713
_refine_ls_number_parameters     416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1545
_refine_ls_R_factor_gt           0.0875
_refine_ls_wR_factor_ref         0.2721
_refine_ls_wR_factor_gt          0.2152
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.32587(17) 0.2885(3) 0.24216(9) 0.0791(7) Uani 1 1 d . . . . .
O2 O 0.10938(19) 0.2801(4) 0.26608(10) 0.1037(9) Uani 1 1 d . . . . .
O3 O -0.0203(3) 0.6582(4) 0.02725(13) 0.1216(11) Uani 1 1 d . . . . .
O4 O 0.1251(3) 0.7059(4) 0.01824(11) 0.1159(11) Uani 1 1 d . . . . .
O5 O 0.83972(18) 0.7052(3) 0.21637(9) 0.0885(8) Uani 1 1 d . . . . .
O6 O 0.68294(18) 0.7415(3) 0.29626(9) 0.0821(7) Uani 1 1 d . . . . .
O7 O 1.0633(3) 0.2801(5) 0.43346(15) 0.1315(12) Uani 1 1 d . . . . .
O8 O 0.9652(2) 0.3313(4) 0.48979(12) 0.1144(11) Uani 1 1 d . . . . .
N1 N 0.28876(18) 0.4364(3) 0.31319(9) 0.0601(6) Uani 1 1 d . . . . .
N2 N 0.0641(3) 0.6492(4) 0.04231(13) 0.0924(10) Uani 1 1 d . . . . .
N3 N 0.69868(17) 0.5843(3) 0.19270(9) 0.0580(6) Uani 1 1 d . . . . .
N4 N 0.9901(3) 0.3388(4) 0.44573(15) 0.0959(10) Uani 1 1 d . . . . .
C1 C 0.3795(2) 0.4559(3) 0.34030(11) 0.0590(7) Uani 1 1 d . . . . .
C2 C 0.4660(2) 0.4149(4) 0.32553(12) 0.0658(8) Uani 1 1 d . . . . .
H2A H 0.472171 0.363768 0.293459 0.079 Uiso 1 1 calc R U . . .
C3 C 0.5429(3) 0.4534(4) 0.36063(15) 0.0767(9) Uani 1 1 d . . . . .
H3A H 0.602068 0.429511 0.351675 0.092 Uiso 1 1 calc R U . . .
C4 C 0.5338(3) 0.5267(5) 0.40875(15) 0.0825(10) Uani 1 1 d . . . . .
H4A H 0.586715 0.550031 0.431669 0.099 Uiso 1 1 calc R U . . .
C5 C 0.4476(3) 0.5654(4) 0.42312(13) 0.0752(9) Uani 1 1 d . . . . .
H5A H 0.441995 0.614461 0.455550 0.090 Uiso 1 1 calc R U . . .
C6 C 0.3688(2) 0.5302(4) 0.38844(11) 0.0603(8) Uani 1 1 d . . . . .
C7 C 0.2705(2) 0.5589(4) 0.39101(12) 0.0676(9) Uani 1 1 d . . . . .
C8 C 0.2296(3) 0.6331(5) 0.43691(15) 0.1003(13) Uani 1 1 d . . . . .
H8A H 0.278704 0.662314 0.463753 0.150 Uiso 1 1 calc R U . . .
H8B H 0.194766 0.731733 0.425860 0.150 Uiso 1 1 calc R U . . .
H8C H 0.189115 0.552740 0.450572 0.150 Uiso 1 1 calc R U . . .
C9 C 0.2251(2) 0.5028(4) 0.34608(13) 0.0691(9) Uani 1 1 d . . . . .
H9A H 0.160876 0.506772 0.337594 0.083 Uiso 1 1 calc R U . . .
C10 C 0.2677(2) 0.3581(4) 0.26607(12) 0.0671(8) Uani 1 1 d . . . . .
C11 C 0.1662(3) 0.3524(4) 0.24210(13) 0.0728(9) Uani 1 1 d . . . . .
C12 C 0.1429(2) 0.4237(4) 0.18899(12) 0.0643(8) Uani 1 1 d . . . . .
C13 C 0.0512(3) 0.4105(4) 0.16549(15) 0.0788(10) Uani 1 1 d . . . . .
H13A H 0.007112 0.353542 0.182541 0.095 Uiso 1 1 calc R U . . .
C14 C 0.0261(3) 0.4822(4) 0.11690(15) 0.0835(11) Uani 1 1 d . . . . .
H14A H -0.034569 0.473458 0.100738 0.100 Uiso 1 1 calc R U . . .
C15 C 0.0922(3) 0.5662(4) 0.09301(13) 0.0744(10) Uani 1 1 d . . . . .
C16 C 0.1837(3) 0.5795(4) 0.11460(13) 0.0730(9) Uani 1 1 d . . . . .
H16A H 0.227471 0.634723 0.096905 0.088 Uiso 1 1 calc R U . . .
C17 C 0.2082(2) 0.5082(4) 0.16334(13) 0.0707(9) Uani 1 1 d . . . . .
H17A H 0.269213 0.516983 0.179058 0.085 Uiso 1 1 calc R U . . .
C21 C 0.7041(2) 0.5659(3) 0.13825(11) 0.0564(7) Uani 1 1 d . . . . .
C22 C 0.7748(2) 0.6056(4) 0.10805(12) 0.0665(8) Uani 1 1 d . . . . .
H22A H 0.829927 0.655288 0.122677 0.080 Uiso 1 1 calc R U . . .
C23 C 0.7594(3) 0.5677(5) 0.05487(14) 0.0819(10) Uani 1 1 d . . . . .
H23A H 0.805370 0.591753 0.033354 0.098 Uiso 1 1 calc R U . . .
C24 C 0.6773(3) 0.4951(5) 0.03327(14) 0.0863(11) Uani 1 1 d . . . . .
H24A H 0.669058 0.471575 -0.002513 0.104 Uiso 1 1 calc R U . . .
C25 C 0.6076(2) 0.4569(4) 0.06340(13) 0.0711(9) Uani 1 1 d . . . . .
H25A H 0.552430 0.408367 0.048396 0.085 Uiso 1 1 calc R U . . .
C26 C 0.6209(2) 0.4920(3) 0.11641(12) 0.0594(7) Uani 1 1 d . . . . .
C27 C 0.5631(2) 0.4651(4) 0.15894(13) 0.0665(8) Uani 1 1 d . . . . .
C28 C 0.4690(3) 0.3868(5) 0.15218(16) 0.0962(12) Uani 1 1 d . . . . .
H28A H 0.452266 0.360033 0.115804 0.144 Uiso 1 1 calc R U . . .
H28B H 0.469705 0.286111 0.172767 0.144 Uiso 1 1 calc R U . . .
H28C H 0.424306 0.463677 0.163620 0.144 Uiso 1 1 calc R U . . .
C29 C 0.6117(2) 0.5203(4) 0.20284(13) 0.0639(8) Uani 1 1 d . . . . .
H29A H 0.590852 0.516988 0.235888 0.077 Uiso 1 1 calc R U . . .
C31 C 0.7671(2) 0.6493(4) 0.22803(12) 0.0642(8) Uani 1 1 d . . . . .
C32 C 0.7484(2) 0.6582(4) 0.28523(12) 0.0648(8) Uani 1 1 d . . . . .
C33 C 0.8141(2) 0.5757(4) 0.32571(12) 0.0634(8) Uani 1 1 d . . . . .
C34 C 0.7980(2) 0.5928(4) 0.37874(12) 0.0695(9) Uani 1 1 d . . . . .
H34A H 0.748076 0.656326 0.387562 0.083 Uiso 1 1 calc R U . . .
C35 C 0.8564(3) 0.5148(4) 0.41731(13) 0.0768(10) Uani 1 1 d . . . . .
H35A H 0.846355 0.524914 0.452409 0.092 Uiso 1 1 calc R U . . .
C36 C 0.9291(3) 0.4230(4) 0.40361(13) 0.0727(9) Uani 1 1 d . . . . .
C37 C 0.9470(2) 0.4042(4) 0.35228(15) 0.0760(9) Uani 1 1 d . . . . .
H37A H 0.997323 0.340710 0.344107 0.091 Uiso 1 1 calc R U . . .
C38 C 0.8888(2) 0.4814(4) 0.31326(13) 0.0690(8) Uani 1 1 d . . . . .
H38A H 0.899818 0.470022 0.278352 0.083 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.226(4) . ?
O2 C11 1.224(4) . ?
O3 N2 1.241(5) . ?
O4 N2 1.219(4) . ?
O5 C31 1.208(4) . ?
O6 C32 1.215(4) . ?
O7 N4 1.230(5) . ?
O8 N4 1.224(4) . ?
N1 C10 1.363(4) . ?
N1 C9 1.418(4) . ?
N1 C1 1.423(4) . ?
N2 C15 1.473(5) . ?
N3 C31 1.366(4) . ?
N3 C29 1.408(4) . ?
N3 C21 1.413(3) . ?
N4 C36 1.477(5) . ?
C1 C2 1.386(4) . ?
C1 C6 1.392(4) . ?
C2 C3 1.383(5) . ?
C3 C4 1.384(5) . ?
C4 C5 1.372(5) . ?
C5 C6 1.393(5) . ?
C6 C7 1.448(5) . ?
C7 C9 1.337(5) . ?
C7 C8 1.496(4) . ?
C10 C11 1.526(5) . ?
C11 C12 1.478(5) . ?
C12 C17 1.384(5) . ?
C12 C13 1.398(5) . ?
C13 C14 1.381(5) . ?
C14 C15 1.367(5) . ?
C15 C16 1.379(5) . ?
C16 C17 1.382(5) . ?
C21 C22 1.386(4) . ?
C21 C26 1.399(4) . ?
C22 C23 1.389(4) . ?
C23 C24 1.380(5) . ?
C24 C25 1.370(5) . ?
C25 C26 1.378(4) . ?
C26 C27 1.460(4) . ?
C27 C29 1.332(4) . ?
C27 C28 1.490(5) . ?
C31 C32 1.521(4) . ?
C32 C33 1.480(4) . ?
C33 C38 1.382(5) . ?
C33 C34 1.410(4) . ?
C34 C35 1.375(5) . ?
C35 C36 1.358(5) . ?
C36 C37 1.376(5) . ?
C37 C38 1.377(5) . ?

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
C10 N1 C9 127.0(3) . . ?
C10 N1 C1 125.8(3) . . ?
C9 N1 C1 107.1(2) . . ?
O4 N2 O3 124.3(4) . . ?
O4 N2 C15 117.9(4) . . ?
O3 N2 C15 117.7(4) . . ?
C31 N3 C29 127.7(3) . . ?
C31 N3 C21 125.3(3) . . ?
C29 N3 C21 107.1(2) . . ?
O8 N4 O7 124.6(4) . . ?
O8 N4 C36 118.8(4) . . ?
O7 N4 C36 116.6(4) . . ?
C2 C1 C6 122.4(3) . . ?
C2 C1 N1 130.7(3) . . ?
C6 C1 N1 106.9(3) . . ?
C3 C2 C1 117.0(3) . . ?
C2 C3 C4 121.5(3) . . ?
C5 C4 C3 120.9(3) . . ?
C4 C5 C6 119.0(3) . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 132.5(3) . . ?
C1 C6 C7 108.3(3) . . ?
C9 C7 C6 107.4(3) . . ?
C9 C7 C8 127.5(3) . . ?
C6 C7 C8 125.1(3) . . ?
C7 C9 N1 110.3(3) . . ?
O1 C10 N1 123.5(3) . . ?
O1 C10 C11 117.8(3) . . ?
N1 C10 C11 118.6(3) . . ?
O2 C11 C12 123.1(3) . . ?
O2 C11 C10 118.8(3) . . ?
C12 C11 C10 118.0(3) . . ?
C17 C12 C13 119.8(3) . . ?
C17 C12 C11 121.8(3) . . ?
C13 C12 C11 118.4(3) . . ?
C14 C13 C12 119.8(4) . . ?
C15 C14 C13 118.7(4) . . ?
C14 C15 C16 123.0(3) . . ?
C14 C15 N2 118.5(4) . . ?
C16 C15 N2 118.5(4) . . ?
C15 C16 C17 118.0(3) . . ?
C12 C17 C16 120.6(3) . . ?
C22 C21 C26 121.9(3) . . ?
C22 C21 N3 130.8(3) . . ?
C26 C21 N3 107.3(3) . . ?
C21 C22 C23 116.7(3) . . ?
C24 C23 C22 121.4(3) . . ?
C25 C24 C23 121.4(3) . . ?
C24 C25 C26 118.7(3) . . ?
C25 C26 C21 119.9(3) . . ?
C25 C26 C27 132.6(3) . . ?
C21 C26 C27 107.5(3) . . ?
C29 C27 C26 106.9(3) . . ?
C29 C27 C28 128.7(3) . . ?
C26 C27 C28 124.4(3) . . ?
C27 C29 N3 111.2(3) . . ?
O5 C31 N3 124.1(3) . . ?
O5 C31 C32 118.3(3) . . ?
N3 C31 C32 117.5(3) . . ?
O6 C32 C33 122.4(3) . . ?
O6 C32 C31 118.4(3) . . ?
C33 C32 C31 119.0(3) . . ?
C38 C33 C34 119.5(3) . . ?
C38 C33 C32 122.5(3) . . ?
C34 C33 C32 118.0(3) . . ?
C35 C34 C33 119.6(4) . . ?
C36 C35 C34 119.3(3) . . ?
C35 C36 C37 122.6(3) . . ?
C35 C36 N4 118.2(4) . . ?
C37 C36 N4 119.2(4) . . ?
C36 C37 C38 118.7(4) . . ?
C33 C38 C37 120.3(3) . . ?

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.223

####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1847721'
_audit_update_record             
;
2018-08-12 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H24 Br2 N2 O4'
_chemical_formula_weight         684.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.222(9)
_cell_length_b                   10.455(8)
_cell_length_c                   13.216(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.726(13)
_cell_angle_gamma                90
_cell_volume                     1500(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4263
_cell_measurement_theta_min      2.5144
_cell_measurement_theta_max      27.4314

_exptl_crystal_description       Bloc
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    2.744
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.367
_exptl_absorpt_correction_T_max  0.464
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12750
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.188
_diffrn_reflns_theta_max         27.444
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3379
_reflns_number_gt                2859
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1116P)²+0.5248P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3379
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.2026
_refine_ls_wR_factor_gt          0.1926
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.30904(5) 0.20977(4) 0.07045(3) 0.0800(3) Uani 1 1 d . . . . .
O1 O 0.4949(3) -0.0732(3) -0.3721(2) 0.0601(6) Uani 1 1 d . . . . .
O2 O 0.3717(3) -0.2791(2) -0.2621(2) 0.0683(8) Uani 1 1 d . . . . .
N1 N 0.3076(3) -0.0378(3) -0.5520(2) 0.0482(6) Uani 1 1 d . . . . .
H1A H 0.377021 -0.007834 -0.557730 0.058 Uiso 1 1 calc R U . . .
C1 C 0.2009(3) -0.0357(3) -0.6283(3) 0.0512(7) Uani 1 1 d . . . . .
C2 C 0.1764(4) 0.0145(4) -0.7299(3) 0.0641(10) Uani 1 1 d . . . . .
H2A H 0.237404 0.054816 -0.754550 0.077 Uiso 1 1 calc R U . . .
C3 C 0.0597(5) 0.0017(5) -0.7907(4) 0.0789(13) Uani 1 1 d . . . . .
H3A H 0.040426 0.035031 -0.858150 0.095 Uiso 1 1 calc R U . . .
C4 C -0.0326(5) -0.0600(5) -0.7551(4) 0.0867(15) Uani 1 1 d . . . . .
H4A H -0.111161 -0.067323 -0.799564 0.104 Uiso 1 1 calc R U . . .
C5 C -0.0098(4) -0.1100(5) -0.6560(4) 0.0778(12) Uani 1 1 d . . . . .
H5A H -0.071503 -0.151990 -0.633571 0.093 Uiso 1 1 calc R U . . .
C6 C 0.1091(4) -0.0964(3) -0.5889(3) 0.0559(8) Uani 1 1 d . . . . .
C7 C 0.1645(3) -0.1337(3) -0.4835(3) 0.0524(7) Uani 1 1 d . . . . .
C8 C 0.0990(5) -0.2035(4) -0.4148(4) 0.0724(12) Uani 1 1 d . . . . .
H8A H 0.014286 -0.215623 -0.451547 0.109 Uiso 1 1 calc R U . . .
H8B H 0.137295 -0.285309 -0.396226 0.109 Uiso 1 1 calc R U . . .
H8C H 0.103544 -0.154538 -0.352512 0.109 Uiso 1 1 calc R U . . .
C9 C 0.2877(3) -0.0954(3) -0.4634(3) 0.0468(7) Uani 1 1 d . . . . .
C10 C 0.3901(3) -0.1067(3) -0.3723(3) 0.0480(7) Uani 1 1 d . . . . .
C11 C 0.3731(3) -0.1636(3) -0.2709(3) 0.0493(7) Uani 1 1 d . . . . .
C12 C 0.3629(3) -0.0730(3) -0.1868(2) 0.0447(7) Uani 1 1 d . . . . .
C13 C 0.3336(4) -0.1188(3) -0.0970(3) 0.0570(9) Uani 1 1 d . . . . .
H13A H 0.323721 -0.206244 -0.089168 0.068 Uiso 1 1 calc R U . . .
C14 C 0.3192(4) -0.0359(4) -0.0194(3) 0.0615(9) Uani 1 1 d . . . . .
H14A H 0.300044 -0.066887 0.040583 0.074 Uiso 1 1 calc R U . . .
C15 C 0.3336(3) 0.0931(3) -0.0326(3) 0.0514(7) Uani 1 1 d . . . . .
C16 C 0.3653(4) 0.1415(3) -0.1193(3) 0.0589(9) Uani 1 1 d . . . . .
H16A H 0.376501 0.228906 -0.126011 0.071 Uiso 1 1 calc R U . . .
C17 C 0.3802(4) 0.0573(3) -0.1963(3) 0.0522(8) Uani 1 1 d . . . . .
H17A H 0.401946 0.088663 -0.254997 0.063 Uiso 1 1 calc R U . . .


_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 C15 1.900(4) . ?
O1 C10 1.227(4) . ?
O2 C11 1.214(4) . ?
N1 C1 1.356(5) . ?
N1 C9 1.385(4) . ?
C1 C2 1.402(5) . ?
C1 C6 1.416(5) . ?
C2 C3 1.358(7) . ?
C3 C4 1.399(8) . ?
C4 C5 1.372(7) . ?
C5 C6 1.409(6) . ?
C6 C7 1.427(5) . ?
C7 C9 1.399(5) . ?
C7 C8 1.496(5) . ?
C9 C10 1.442(5) . ?
C10 C11 1.522(5) . ?
C11 C12 1.486(4) . ?
C12 C17 1.387(4) . ?
C12 C13 1.394(4) . ?
C13 C14 1.383(5) . ?
C14 C15 1.375(5) . ?
C15 C16 1.379(5) . ?
C16 C17 1.387(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 109.5(3) . . ?
N1 C1 C2 129.7(4) . . ?
N1 C1 C6 107.9(3) . . ?
C2 C1 C6 122.5(4) . . ?
C3 C2 C1 117.0(4) . . ?
C2 C3 C4 122.1(4) . . ?
C5 C4 C3 121.5(5) . . ?
C4 C5 C6 118.6(5) . . ?
C5 C6 C1 118.3(4) . . ?
C5 C6 C7 134.0(4) . . ?
C1 C6 C7 107.7(3) . . ?
C9 C7 C6 105.8(3) . . ?
C9 C7 C8 129.7(4) . . ?
C6 C7 C8 124.5(4) . . ?
N1 C9 C7 109.1(3) . . ?
N1 C9 C10 118.4(3) . . ?
C7 C9 C10 132.4(3) . . ?
O1 C10 C9 122.5(3) . . ?
O1 C10 C11 116.4(3) . . ?
C9 C10 C11 121.0(3) . . ?
O2 C11 C12 123.8(3) . . ?
O2 C11 C10 118.7(3) . . ?
C12 C11 C10 117.4(3) . . ?
C17 C12 C13 118.9(3) . . ?
C17 C12 C11 121.3(3) . . ?
C13 C12 C11 119.9(3) . . ?
C14 C13 C12 120.9(3) . . ?
C15 C14 C13 118.7(3) . . ?
C14 C15 C16 122.0(3) . . ?
C14 C15 Br1 119.7(3) . . ?
C16 C15 Br1 118.4(3) . . ?
C15 C16 C17 118.8(3) . . ?
C16 C17 C12 120.7(3) . . ?

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.086

