# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_d18675
_database_code_depnum_ccdc_archive 'CCDC 1819727'
_audit_update_record             
;
2018-01-26 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H23 Br N2 O6'
_chemical_formula_sum            'C27 H23 Br N2 O6'
_chemical_formula_weight         551.38

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'

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

_cell_length_a                   16.1053(13)
_cell_length_b                   20.5425(16)
_cell_length_c                   16.5420(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5472.8(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3195
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      23.86

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2256
_exptl_absorpt_coefficient_mu    1.543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7903
_exptl_absorpt_correction_T_max  0.9698
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            35238
_diffrn_reflns_av_R_equivalents  0.1473
_diffrn_reflns_av_sigmaI/netI    0.0998
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.03
_reflns_number_total             4835
_reflns_number_gt                3270
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0197P)²+15.3504P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4835
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.0887
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6821(3) 0.7841(3) 0.8391(3) 0.0278(14) Uani 1 1 d . . .
C2 C 0.7089(4) 0.7840(3) 0.9176(4) 0.0411(17) Uani 1 1 d . . .
H2 H 0.6879 0.8150 0.9550 0.049 Uiso 1 1 calc R . .
C3 C 0.7663(4) 0.7387(4) 0.9419(4) 0.054(2) Uani 1 1 d . . .
H3 H 0.7852 0.7379 0.9963 0.064 Uiso 1 1 calc R . .
C4 C 0.7960(4) 0.6946(3) 0.8870(4) 0.0488(19) Uani 1 1 d . . .
H4 H 0.8371 0.6641 0.9031 0.059 Uiso 1 1 calc R . .
C5 C 0.7671(4) 0.6940(3) 0.8087(4) 0.0380(16) Uani 1 1 d . . .
H5 H 0.7875 0.6624 0.7717 0.046 Uiso 1 1 calc R . .
C6 C 0.7090(3) 0.7386(3) 0.7834(3) 0.0214(12) Uani 1 1 d . . .
C7 C 0.6754(3) 0.7347(3) 0.6993(3) 0.0192(12) Uani 1 1 d . . .
C8 C 0.5089(3) 0.6919(3) 0.6088(3) 0.0224(13) Uani 1 1 d . . .
H8 H 0.5072 0.7345 0.6380 0.027 Uiso 1 1 calc R . .
C9 C 0.4828(3) 0.7038(3) 0.5227(3) 0.0208(12) Uani 1 1 d . . .
C10 C 0.5108(4) 0.7570(3) 0.4793(3) 0.0293(14) Uani 1 1 d . . .
H10 H 0.5515 0.7849 0.5023 0.035 Uiso 1 1 calc R . .
C11 C 0.4804(4) 0.7700(3) 0.4031(4) 0.0401(17) Uani 1 1 d . . .
H11 H 0.5011 0.8059 0.3731 0.048 Uiso 1 1 calc R . .
C12 C 0.4196(4) 0.7303(3) 0.3706(4) 0.0429(17) Uani 1 1 d . . .
H12 H 0.3967 0.7405 0.3192 0.051 Uiso 1 1 calc R . .
C13 C 0.3918(4) 0.6765(3) 0.4115(3) 0.0341(15) Uani 1 1 d . . .
H13 H 0.3510 0.6488 0.3882 0.041 Uiso 1 1 calc R . .
C14 C 0.4242(3) 0.6629(3) 0.4876(3) 0.0244(13) Uani 1 1 d . . .
C15 C 0.4434(3) 0.5932(3) 0.5981(3) 0.0235(13) Uani 1 1 d . . .
C16 C 0.3904(3) 0.5451(3) 0.6455(3) 0.0246(13) Uani 1 1 d . . .
C17 C 0.3331(4) 0.4379(3) 0.6392(4) 0.0476(19) Uani 1 1 d . . .
H17A H 0.2966 0.4556 0.6821 0.057 Uiso 1 1 calc R . .
H17B H 0.2974 0.4178 0.5973 0.057 Uiso 1 1 calc R . .
C18 C 0.3872(6) 0.3888(4) 0.6734(6) 0.097(3) Uani 1 1 d . . .
H18A H 0.4233 0.3713 0.6310 0.146 Uiso 1 1 calc R . .
H18B H 0.3535 0.3536 0.6964 0.146 Uiso 1 1 calc R . .
H18C H 0.4213 0.4084 0.7161 0.146 Uiso 1 1 calc R . .
C19 C 0.5271(3) 0.5671(3) 0.5778(3) 0.0185(12) Uani 1 1 d . . .
H19 H 0.5306 0.5258 0.5520 0.022 Uiso 1 1 calc R . .
C20 C 0.5977(3) 0.5990(2) 0.5942(3) 0.0172(11) Uani 1 1 d . . .
C21 C 0.6815(3) 0.5711(3) 0.5895(3) 0.0196(12) Uani 1 1 d . . .
C22 C 0.6943(4) 0.5039(3) 0.5933(3) 0.0305(14) Uani 1 1 d . . .
H22 H 0.6479 0.4762 0.6018 0.037 Uiso 1 1 calc R . .
C23 C 0.7715(4) 0.4766(3) 0.5852(4) 0.0352(15) Uani 1 1 d . . .
H23 H 0.7779 0.4306 0.5871 0.042 Uiso 1 1 calc R . .
C24 C 0.8401(4) 0.5160(3) 0.5744(4) 0.0349(15) Uani 1 1 d . . .
C25 C 0.9331(5) 0.4258(3) 0.5648(5) 0.059(2) Uani 1 1 d . . .
H25A H 0.9129 0.4069 0.6155 0.089 Uiso 1 1 calc R . .
H25B H 0.9926 0.4169 0.5591 0.089 Uiso 1 1 calc R . .
H25C H 0.9031 0.4064 0.5192 0.089 Uiso 1 1 calc R . .
C26 C 0.8293(3) 0.5832(3) 0.5725(4) 0.0303(14) Uani 1 1 d . . .
H26 H 0.8763 0.6108 0.5662 0.036 Uiso 1 1 calc R . .
C27 C 0.7515(3) 0.6102(3) 0.5796(3) 0.0243(13) Uani 1 1 d . . .
H27 H 0.7453 0.6562 0.5778 0.029 Uiso 1 1 calc R . .
Br1 Br 0.60067(5) 0.84645(4) 0.80819(5) 0.0547(3) Uani 1 1 d . . .
N1 N 0.6299(2) 0.6797(2) 0.6902(2) 0.0199(10) Uani 1 1 d . . .
N2 N 0.5921(2) 0.66618(19) 0.6156(2) 0.0167(10) Uani 1 1 d . . .
O1 O 0.6860(3) 0.77498(18) 0.6467(2) 0.0340(10) Uani 1 1 d . . .
O2 O 0.4489(2) 0.64885(17) 0.6463(2) 0.0227(8) Uani 1 1 d . . .
O3 O 0.3949(2) 0.60844(18) 0.5266(2) 0.0269(9) Uani 1 1 d . . .
O4 O 0.3635(3) 0.5546(2) 0.7111(3) 0.0472(12) Uani 1 1 d . . .
O5 O 0.3811(3) 0.4908(2) 0.6033(2) 0.0399(11) Uani 1 1 d . . .
O6 O 0.9195(2) 0.4945(2) 0.5655(3) 0.0498(12) Uani 1 1 d . . .
H1' H 0.6167 0.6533 0.7329 0.060 Uiso 1 1 d 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
C1 C2 1.369(8) . ?
C1 C6 1.381(7) . ?
C1 Br1 1.903(6) . ?
C2 C3 1.373(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.369(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.496(7) . ?
C7 O1 1.213(6) . ?
C7 N1 1.355(6) . ?
C8 N2 1.445(6) . ?
C8 O2 1.450(6) . ?
C8 C9 1.505(7) . ?
C8 H8 1.0000 . ?
C9 C10 1.384(7) . ?
C9 C14 1.390(7) . ?
C10 C11 1.379(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.372(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(7) . ?
C13 H13 0.9500 . ?
C14 O3 1.375(6) . ?
C15 O2 1.397(6) . ?
C15 O3 1.450(6) . ?
C15 C19 1.490(7) . ?
C15 C16 1.525(8) . ?
C16 O4 1.184(6) . ?
C16 O5 1.324(6) . ?
C17 C18 1.448(10) . ?
C17 O5 1.460(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.341(7) . ?
C19 H19 0.9500 . ?
C20 N2 1.428(6) . ?
C20 C21 1.467(7) . ?
C21 C27 1.393(7) . ?
C21 C22 1.398(7) . ?
C22 C23 1.371(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(8) . ?
C23 H23 0.9500 . ?
C24 O6 1.362(7) . ?
C24 C26 1.391(8) . ?
C25 O6 1.428(7) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.376(7) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
N1 N2 1.404(5) . ?
N1 H1' 0.9162 . ?

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
C2 C1 C6 122.2(6) . . ?
C2 C1 Br1 118.2(5) . . ?
C6 C1 Br1 119.5(4) . . ?
C1 C2 C3 119.4(6) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 119.3(6) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.9(6) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.6(6) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 117.6(5) . . ?
C5 C6 C7 119.5(5) . . ?
C1 C6 C7 122.8(5) . . ?
O1 C7 N1 124.4(5) . . ?
O1 C7 C6 125.5(5) . . ?
N1 C7 C6 110.1(4) . . ?
N2 C8 O2 111.2(4) . . ?
N2 C8 C9 113.1(4) . . ?
O2 C8 C9 108.6(4) . . ?
N2 C8 H8 107.9 . . ?
O2 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
C10 C9 C14 118.8(5) . . ?
C10 C9 C8 121.9(5) . . ?
C14 C9 C8 119.1(5) . . ?
C11 C10 C9 120.7(6) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.6(6) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.9(6) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 119.1(6) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
O3 C14 C13 117.3(5) . . ?
O3 C14 C9 121.9(5) . . ?
C13 C14 C9 120.8(5) . . ?
O2 C15 O3 108.9(4) . . ?
O2 C15 C19 111.5(4) . . ?
O3 C15 C19 112.4(4) . . ?
O2 C15 C16 105.8(4) . . ?
O3 C15 C16 105.0(4) . . ?
C19 C15 C16 112.9(5) . . ?
O4 C16 O5 125.5(5) . . ?
O4 C16 C15 124.7(5) . . ?
O5 C16 C15 109.7(4) . . ?
C18 C17 O5 111.0(6) . . ?
C18 C17 H17A 109.4 . . ?
O5 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
O5 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C15 123.1(5) . . ?
C20 C19 H19 118.5 . . ?
C15 C19 H19 118.5 . . ?
C19 C20 N2 118.0(5) . . ?
C19 C20 C21 125.4(5) . . ?
N2 C20 C21 116.6(4) . . ?
C27 C21 C22 117.1(5) . . ?
C27 C21 C20 121.7(5) . . ?
C22 C21 C20 121.2(5) . . ?
C23 C22 C21 122.3(5) . . ?
C23 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
C22 C23 C24 119.8(6) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
O6 C24 C23 125.0(6) . . ?
O6 C24 C26 115.9(5) . . ?
C23 C24 C26 119.1(5) . . ?
O6 C25 H25A 109.5 . . ?
O6 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O6 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C24 120.7(5) . . ?
C27 C26 H26 119.6 . . ?
C24 C26 H26 119.6 . . ?
C26 C27 C21 121.0(5) . . ?
C26 C27 H27 119.5 . . ?
C21 C27 H27 119.5 . . ?
C7 N1 N2 119.8(4) . . ?
C7 N1 H1' 122.3 . . ?
N2 N1 H1' 117.4 . . ?
N1 N2 C20 112.5(4) . . ?
N1 N2 C8 113.4(4) . . ?
C20 N2 C8 113.1(4) . . ?
C15 O2 C8 107.3(4) . . ?
C14 O3 C15 112.0(4) . . ?
C16 O5 C17 118.1(5) . . ?
C24 O6 C25 117.8(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.076

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.461 0.250 169.3 24.6
2 0.000 0.539 0.750 169.3 24.2
3 0.500 0.961 0.250 169.3 24.9
4 0.500 0.039 0.750 169.3 24.3
_platon_squeeze_details          
;
;
