# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_123
_database_code_depnum_ccdc_archive 'CCDC 1841972'
loop_
_audit_author_name
_audit_author_address
lyj
;hznu
China
;
_audit_update_record             
;
2018-05-08 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 Br I N O5'
_chemical_formula_weight         573.18

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'
I I -0.4742 1.8119 '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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   5.9203(13)
_cell_length_b                   18.197(4)
_cell_length_c                   19.707(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2123.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1124
_exptl_absorpt_coefficient_mu    3.423
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15740
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         27.44
_reflns_number_total             4836
_reflns_number_gt                4190
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0359P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.023(10)
_refine_ls_number_reflns         4836
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0712
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
I1 I 1.02948(4) 0.684335(12) 0.468744(12) 0.05589(8) Uani 1 1 d . . .
Br1 Br 1.08682(8) 0.57856(2) -0.00233(2) 0.06673(13) Uani 1 1 d . . .
O1 O 0.2802(5) 0.46083(17) 0.28617(18) 0.0737(9) Uani 1 1 d . . .
O2 O 0.9612(5) 0.24772(16) 0.21844(15) 0.0693(8) Uani 1 1 d . . .
O3 O 0.7785(5) 0.16259(15) 0.27869(15) 0.0584(7) Uani 1 1 d . . .
O4 O 0.4544(5) 0.25364(18) 0.39810(13) 0.0737(8) Uani 1 1 d . . .
O5 O 0.7853(4) 0.30419(14) 0.37107(11) 0.0501(6) Uani 1 1 d . . .
N1 N 0.5451(7) 0.29896(16) 0.16984(14) 0.0597(8) Uani 1 1 d . . .
H1A H 0.6695 0.2911 0.1446 1.2(4) Uiso 1 1 d R . .
H1B H 0.4244 0.2845 0.1455 0.38(9) Uiso 1 1 d R . .
C2 C 0.9433(6) 0.53827(17) 0.40037(17) 0.0461(7) Uani 1 1 d . . .
H2 H 1.0843 0.5267 0.4182 0.059(11) Uiso 1 1 d R . .
C3 C 0.6171(5) 0.50419(16) 0.33493(15) 0.0371(6) Uani 1 1 d . . .
C4 C 0.9133(6) 0.5162(2) 0.05469(15) 0.0474(8) Uani 1 1 d . . .
C5 C 0.4956(5) 0.31134(16) 0.28981(15) 0.0443(7) Uani 1 1 d . . .
H5 H 0.3307 0.3160 0.2908 0.049(9) Uiso 1 1 d R . .
C6 C 0.4819(6) 0.45070(18) 0.29412(17) 0.0471(7) Uani 1 1 d . . .
C7 C 0.7902(7) 0.2233(2) 0.24131(16) 0.0474(8) Uani 1 1 d . . .
C8 C 0.6634(6) 0.42584(19) 0.13985(16) 0.0440(7) Uani 1 1 d . . .
C9 C 0.8471(6) 0.60595(17) 0.41313(15) 0.0412(7) Uani 1 1 d . . .
C10 C 0.6355(7) 0.62278(18) 0.38797(18) 0.0503(8) Uani 1 1 d . . .
H10 H 0.5704 0.6682 0.3971 0.043(9) Uiso 1 1 d R . .
C11 C 0.5230(7) 0.37771(18) 0.18590(15) 0.0484(8) Uani 1 1 d . . .
H11 H 0.3641 0.3920 0.1813 0.027(8) Uiso 1 1 d R . .
C12 C 0.5693(6) 0.28665(19) 0.35934(16) 0.0451(7) Uani 1 1 d . . .
C14 C 0.7062(7) 0.5403(2) 0.0784(2) 0.0559(9) Uani 1 1 d . . .
H14 H 0.6511 0.5863 0.0663 0.080(14) Uiso 1 1 d R . .
C15 C 0.8734(7) 0.4044(2) 0.11493(19) 0.0580(10) Uani 1 1 d . . .
H15 H 0.9311 0.3587 0.1271 0.076(13) Uiso 1 1 d R . .
C16 C 0.8297(6) 0.48801(18) 0.36086(17) 0.0430(7) Uani 1 1 d . . .
H16 H 0.8957 0.4428 0.3514 0.055(10) Uiso 1 1 d R . .
C17 C 0.5562(7) 0.25604(18) 0.23228(16) 0.0463(8) Uani 1 1 d . . .
H17 H 0.4436 0.2166 0.2309 0.046(9) Uiso 1 1 d R . .
C18 C 0.5224(6) 0.57220(18) 0.34968(16) 0.0470(7) Uani 1 1 d . . .
H18 H 0.3794 0.5835 0.3332 0.089(16) Uiso 1 1 d R . .
C19 C 0.5847(7) 0.4948(2) 0.12049(19) 0.0546(9) Uani 1 1 d . . .
H19 H 0.4448 0.5105 0.1363 0.058(11) Uiso 1 1 d R . .
C20 C 0.9973(7) 0.44898(19) 0.07243(17) 0.0562(9) Uani 1 1 d . . .
H20 H 1.1367 0.4335 0.0560 0.058(11) Uiso 1 1 d R . .
C21 C 0.5906(6) 0.38393(17) 0.26208(15) 0.0419(7) Uani 1 1 d . . .
H21 H 0.7552 0.3857 0.2671 0.041(9) Uiso 1 1 d R . .
C23 C 0.8774(8) 0.2808(3) 0.4346(2) 0.0693(12) Uani 1 1 d . . .
H23A H 0.8052 0.3071 0.4708 0.13(2) Uiso 1 1 d R . .
H23B H 1.0369 0.2902 0.4356 0.11(2) Uiso 1 1 d R . .
H23C H 0.8510 0.2291 0.4400 0.11(2) Uiso 1 1 d R . .
C24 C 0.9924(9) 0.1267(3) 0.2917(3) 0.0776(13) Uani 1 1 d . . .
H24A H 1.0637 0.1146 0.2494 0.11(2) Uiso 1 1 d R . .
H24B H 0.9668 0.0825 0.3173 0.108(18) Uiso 1 1 d R . .
H24C H 1.0884 0.1590 0.3172 0.102(19) 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
I1 C9 2.098(3) . ?
Br1 C4 1.899(4) . ?
O1 C6 1.218(5) . ?
O2 C7 1.194(5) . ?
O3 C7 1.330(4) . ?
O3 C24 1.448(5) . ?
O4 C12 1.186(4) . ?
O5 C12 1.338(4) . ?
O5 C23 1.430(4) . ?
N1 C17 1.459(4) . ?
N1 C11 1.473(4) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9001 . ?
C2 C16 1.377(5) . ?
C2 C9 1.380(4) . ?
C2 H2 0.9301 . ?
C3 C18 1.389(4) . ?
C3 C16 1.390(5) . ?
C3 C6 1.495(5) . ?
C4 C20 1.365(5) . ?
C4 C14 1.383(5) . ?
C5 C12 1.507(5) . ?
C5 C21 1.536(4) . ?
C5 C17 1.558(4) . ?
C5 H5 0.9800 . ?
C6 C21 1.513(5) . ?
C7 C17 1.518(5) . ?
C8 C19 1.392(5) . ?
C8 C15 1.393(5) . ?
C8 C11 1.511(5) . ?
C9 C10 1.382(5) . ?
C10 C18 1.365(5) . ?
C10 H10 0.9299 . ?
C11 C21 1.558(4) . ?
C11 H11 0.9800 . ?
C14 C19 1.375(5) . ?
C14 H14 0.9300 . ?
C15 C20 1.378(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17 0.9801 . ?
C18 H18 0.9299 . ?
C19 H19 0.9300 . ?
C20 H20 0.9301 . ?
C21 H21 0.9800 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9599 . ?
C24 H24A 0.9601 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O3 C24 115.3(3) . . ?
C12 O5 C23 116.4(3) . . ?
C17 N1 C11 110.1(2) . . ?
C17 N1 H1A 110.1 . . ?
C11 N1 H1A 110.2 . . ?
C17 N1 H1B 109.2 . . ?
C11 N1 H1B 109.2 . . ?
H1A N1 H1B 108.0 . . ?
C16 C2 C9 119.6(3) . . ?
C16 C2 H2 120.2 . . ?
C9 C2 H2 120.2 . . ?
C18 C3 C16 118.5(3) . . ?
C18 C3 C6 118.5(3) . . ?
C16 C3 C6 123.0(3) . . ?
C20 C4 C14 121.4(3) . . ?
C20 C4 Br1 119.3(3) . . ?
C14 C4 Br1 119.3(3) . . ?
C12 C5 C21 118.3(3) . . ?
C12 C5 C17 113.7(3) . . ?
C21 C5 C17 102.3(2) . . ?
C12 C5 H5 107.2 . . ?
C21 C5 H5 107.3 . . ?
C17 C5 H5 107.4 . . ?
O1 C6 C3 119.7(3) . . ?
O1 C6 C21 119.0(3) . . ?
C3 C6 C21 121.3(3) . . ?
O2 C7 O3 124.2(4) . . ?
O2 C7 C17 125.7(3) . . ?
O3 C7 C17 110.1(3) . . ?
C19 C8 C15 117.1(3) . . ?
C19 C8 C11 120.2(3) . . ?
C15 C8 C11 122.7(3) . . ?
C2 C9 C10 120.5(3) . . ?
C2 C9 I1 119.3(3) . . ?
C10 C9 I1 120.2(2) . . ?
C18 C10 C9 119.6(3) . . ?
C18 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
N1 C11 C8 112.7(3) . . ?
N1 C11 C21 104.8(2) . . ?
C8 C11 C21 113.3(3) . . ?
N1 C11 H11 108.9 . . ?
C8 C11 H11 108.6 . . ?
C21 C11 H11 108.4 . . ?
O4 C12 O5 123.9(3) . . ?
O4 C12 C5 124.8(3) . . ?
O5 C12 C5 111.3(3) . . ?
C19 C14 C4 118.5(4) . . ?
C19 C14 H14 120.8 . . ?
C4 C14 H14 120.7 . . ?
C20 C15 C8 121.6(4) . . ?
C20 C15 H15 119.3 . . ?
C8 C15 H15 119.1 . . ?
C2 C16 C3 120.6(3) . . ?
C2 C16 H16 119.7 . . ?
C3 C16 H16 119.7 . . ?
N1 C17 C7 110.5(3) . . ?
N1 C17 C5 104.9(3) . . ?
C7 C17 C5 112.2(3) . . ?
N1 C17 H17 109.7 . . ?
C7 C17 H17 109.7 . . ?
C5 C17 H17 109.7 . . ?
C10 C18 C3 121.2(3) . . ?
C10 C18 H18 119.4 . . ?
C3 C18 H18 119.4 . . ?
C14 C19 C8 122.2(4) . . ?
C14 C19 H19 119.0 . . ?
C8 C19 H19 118.8 . . ?
C4 C20 C15 119.3(4) . . ?
C4 C20 H20 120.4 . . ?
C15 C20 H20 120.3 . . ?
C6 C21 C5 112.7(3) . . ?
C6 C21 C11 110.6(3) . . ?
C5 C21 C11 100.7(2) . . ?
C6 C21 H21 110.8 . . ?
C5 C21 H21 110.8 . . ?
C11 C21 H21 110.8 . . ?
O5 C23 H23A 109.4 . . ?
O5 C23 H23B 109.9 . . ?
H23A C23 H23B 109.5 . . ?
O5 C23 H23C 109.2 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.4 . . ?
H24A C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.090
