# 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. 
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data_mo_20180288-xht_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1zpkjr
_database_code_depnum_ccdc_archive 'CCDC 1837975'
_audit_update_record             
;
2018-05-05 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;
_audit_creation_date             2018-04-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H17 Br N2 O3'
_chemical_formula_sum            'C24 H17 Br N2 O3'
_chemical_formula_weight         461.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   8.811(3)
_cell_length_b                   20.892(8)
_cell_length_c                   10.950(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.717(12)
_cell_angle_gamma                90
_cell_volume                     1940.3(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2513
_cell_measurement_temperature    173
_cell_measurement_theta_max      23.668
_cell_measurement_theta_min      2.401
_shelx_estimated_absorpt_T_max   0.783
_shelx_estimated_absorpt_T_min   0.584
_exptl_absorpt_coefficient_mu    2.149
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.3894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1238 before and 0.0618 after correction. The Ratio of minimum to maximum transmission is 0.5224. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12115
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.496
_diffrn_reflns_theta_min         2.164
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3009
_reflns_number_total             3940
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.539
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.0040(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3940
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.068
_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)+(0.0541P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1245
_refine_special_details          ?
_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. Uiso/Uaniso restraints and constraints
Uanis(C24) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(O2) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
3.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_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 1.17192(4) 0.61137(2) 0.82142(3) 0.03542(16) Uani 1 1 d . . . . .
O1 O 0.9122(3) 0.33476(12) 0.6821(2) 0.0410(6) Uani 1 1 d . . . . .
O2 O 0.8436(5) 0.39834(13) 0.8206(2) 0.0633(10) Uani 1 1 d . U . . .
O3 O 0.6272(3) 0.57761(12) 0.2246(2) 0.0437(7) Uani 1 1 d . . . . .
N1 N 0.6630(3) 0.50055(13) 0.3823(2) 0.0232(6) Uani 1 1 d . . . . .
N2 N 0.5894(3) 0.44167(13) 0.3996(2) 0.0241(6) Uani 1 1 d . . . . .
C1 C 0.4667(4) 0.48218(16) 0.2062(3) 0.0272(7) Uani 1 1 d . . . . .
C2 C 0.3538(4) 0.48534(18) 0.0896(3) 0.0374(9) Uani 1 1 d . . . . .
H2 H 0.3530 0.5200 0.0333 0.045 Uiso 1 1 calc R . . . .
C3 C 0.2441(4) 0.4375(2) 0.0577(3) 0.0411(9) Uani 1 1 d . . . . .
H3 H 0.1675 0.4383 -0.0223 0.049 Uiso 1 1 calc R . . . .
C4 C 0.2441(4) 0.38756(17) 0.1422(3) 0.0343(8) Uani 1 1 d . . . . .
H4 H 0.1663 0.3551 0.1182 0.041 Uiso 1 1 calc R . . . .
C5 C 0.3529(4) 0.38355(16) 0.2593(3) 0.0307(8) Uani 1 1 d . . . . .
H5 H 0.3502 0.3496 0.3165 0.037 Uiso 1 1 calc R . . . .
C6 C 0.4670(4) 0.43171(16) 0.2899(3) 0.0240(7) Uani 1 1 d . . . . .
C7 C 0.5894(4) 0.52684(16) 0.2636(3) 0.0301(8) Uani 1 1 d . . . . .
C8 C 0.7810(3) 0.52733(15) 0.4845(3) 0.0220(7) Uani 1 1 d . . . . .
C9 C 0.8465(4) 0.58601(16) 0.4716(3) 0.0273(7) Uani 1 1 d . . . . .
H9 H 0.8116 0.6092 0.3944 0.033 Uiso 1 1 calc R . . . .
C10 C 0.9637(4) 0.61108(15) 0.5717(3) 0.0276(7) Uani 1 1 d . . . . .
H10 H 1.0098 0.6514 0.5632 0.033 Uiso 1 1 calc R . . . .
C11 C 1.0126(4) 0.57720(16) 0.6832(3) 0.0257(7) Uani 1 1 d . . . . .
C12 C 0.9486(4) 0.51774(15) 0.6969(3) 0.0251(7) Uani 1 1 d . . . . .
H12 H 0.9845 0.4948 0.7743 0.030 Uiso 1 1 calc R . . . .
C13 C 0.8321(3) 0.49181(15) 0.5975(3) 0.0212(6) Uani 1 1 d . . . . .
C14 C 0.7701(4) 0.42715(15) 0.6015(3) 0.0230(7) Uani 1 1 d . . . . .
C15 C 0.6564(4) 0.40290(15) 0.5035(3) 0.0222(7) Uani 1 1 d . . . . .
C16 C 0.5994(3) 0.33558(15) 0.4998(3) 0.0217(7) Uani 1 1 d . . . . .
C17 C 0.5166(4) 0.31590(16) 0.5841(3) 0.0269(7) Uani 1 1 d . . . . .
H17 H 0.4900 0.3458 0.6403 0.032 Uiso 1 1 calc R . . . .
C18 C 0.4726(4) 0.25240(18) 0.5860(3) 0.0342(8) Uani 1 1 d . . . . .
H18 H 0.4151 0.2391 0.6434 0.041 Uiso 1 1 calc R . . . .
C19 C 0.5112(4) 0.20780(17) 0.5055(3) 0.0333(8) Uani 1 1 d . . . . .
H19 H 0.4807 0.1643 0.5076 0.040 Uiso 1 1 calc R . . . .
C20 C 0.5953(4) 0.22788(17) 0.4215(3) 0.0303(8) Uani 1 1 d . . . . .
H20 H 0.6232 0.1977 0.3663 0.036 Uiso 1 1 calc R . . . .
C21 C 0.6384(4) 0.29109(16) 0.4178(3) 0.0268(7) Uani 1 1 d . . . . .
H21 H 0.6947 0.3045 0.3596 0.032 Uiso 1 1 calc R . . . .
C22 C 0.8435(4) 0.38592(15) 0.7144(3) 0.0276(7) Uani 1 1 d . . . . .
C23 C 0.9830(5) 0.2902(2) 0.7846(4) 0.0579(12) Uani 1 1 d . U . . .
H23A H 0.9857 0.3101 0.8672 0.070 Uiso 1 1 calc R . . . .
H23B H 0.9178 0.2509 0.7754 0.070 Uiso 1 1 calc R . . . .
C24 C 1.1346(6) 0.2741(3) 0.7823(7) 0.093(2) Uani 1 1 d . U . . .
H24A H 1.1339 0.2600 0.6968 0.140 Uiso 1 1 calc GR . . . .
H24B H 1.1740 0.2394 0.8428 0.140 Uiso 1 1 calc GR . . . .
H24C H 1.2034 0.3116 0.8057 0.140 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C11 1.903(3) . ?
O1 C22 1.323(4) . ?
O1 C23 1.462(4) . ?
O2 C22 1.192(4) . ?
O3 C7 1.223(4) . ?
N1 N2 1.427(4) . ?
N1 C7 1.398(4) . ?
N1 C8 1.419(4) . ?
N2 C6 1.395(4) . ?
N2 C15 1.391(4) . ?
C1 C2 1.391(4) . ?
C1 C6 1.396(5) . ?
C1 C7 1.438(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.369(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(5) . ?
C8 C9 1.379(4) . ?
C8 C13 1.408(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(5) . ?
C11 C12 1.389(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(4) . ?
C13 C14 1.462(4) . ?
C14 C15 1.352(4) . ?
C14 C22 1.502(4) . ?
C15 C16 1.490(4) . ?
C16 C17 1.386(4) . ?
C16 C21 1.398(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.393(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(5) . ?
C21 H21 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.384(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C22 O1 C23 116.1(3) . . ?
C7 N1 N2 110.4(2) . . ?
C7 N1 C8 129.3(3) . . ?
C8 N1 N2 119.8(2) . . ?
C6 N2 N1 106.7(2) . . ?
C15 N2 N1 120.2(2) . . ?
C15 N2 C6 132.4(3) . . ?
C2 C1 C6 120.8(3) . . ?
C2 C1 C7 129.5(3) . . ?
C6 C1 C7 109.6(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.5(3) . . ?
C5 C4 H4 118.7 . . ?
C4 C5 H5 121.5 . . ?
C4 C5 C6 116.9(3) . . ?
C6 C5 H5 121.5 . . ?
N2 C6 C1 108.4(3) . . ?
N2 C6 C5 130.7(3) . . ?
C1 C6 C5 120.8(3) . . ?
O3 C7 N1 124.3(3) . . ?
O3 C7 C1 130.8(3) . . ?
N1 C7 C1 104.8(3) . . ?
C9 C8 N1 120.5(3) . . ?
C9 C8 C13 121.1(3) . . ?
C13 C8 N1 118.5(3) . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 Br1 120.0(3) . . ?
C10 C11 C12 121.1(3) . . ?
C12 C11 Br1 118.9(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C14 118.7(3) . . ?
C12 C13 C8 118.4(3) . . ?
C12 C13 C14 122.7(3) . . ?
C13 C14 C22 118.3(3) . . ?
C15 C14 C13 121.7(3) . . ?
C15 C14 C22 119.9(3) . . ?
N2 C15 C16 117.5(3) . . ?
C14 C15 N2 119.3(3) . . ?
C14 C15 C16 123.2(3) . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 C21 119.7(3) . . ?
C21 C16 C15 120.4(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.1(3) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 120.6 . . ?
C18 C19 C20 118.9(3) . . ?
C20 C19 H19 120.6 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.7 . . ?
C16 C21 H21 120.0 . . ?
C20 C21 C16 120.1(3) . . ?
C20 C21 H21 120.0 . . ?
O1 C22 C14 111.7(3) . . ?
O2 C22 O1 123.9(3) . . ?
O2 C22 C14 124.4(3) . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
C24 C23 O1 110.7(4) . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
